Pest control composition including novel iminopyridine derivative

ABSTRACT

Provided is a pest control composition containing a novel iminopyridine derivative and other pest control agents. 
     Provided is a pest control composition containing an iminopyridine derivative represented by the following Formula (I) and at least one of other pest control agents: 
     
       
         
         
             
             
         
       
         
         
           
             [in the formula (I), Ar represents a 5- to 6-membered heterocycle which may be substituted, A represents a heterocycle having a 5- to 10-membered unsaturated bond including one or more nitrogen atoms, and has an imino group substituted with an R group at a position adjacent to the nitrogen atom present on the cycle, Y represents hydrogen, halogen and the like, and R represents any one of groups represented by the following Formulae (a) to (e), (y) or (z)].

This application is a Continuation of U.S. application Ser. No. 14/320,808, filed Jul. 1, 2014, (now allowed); which is a Continuation of PCT/JP2013/056051, filed Feb. 27, 2013; the entire disclosures of each of which are hereby incorporated herein by reference.

BACKGROUND OF THE INVENTION Field of the Invention

The present invention relates to a pest control composition containing a novel iminopyridine derivative and at least one of other pest control agents.

Related Background Art

Although numerous pest control agents have been discovered so far, the development of novel drugs which has high safety is still required in view of the problem of reduction in drug sensitivity, the issue of long-term efficacy, safety to workers or safety in terms of environmental impacts. Further, in agriculture, in order to achieve a reduction in labor for the pest control work, it is general to mix a plurality of components of a chemical for pest control and treat seeds or farm products during the growing seedling period with the chemical, and under these circumstances, it is required to use a long-term residual efficacy type chemical having penetrating and migrating property. In addition, it is also possible to solve problems such as scattering of a chemical to the surrounding environment outside agricultural land or exposure to a person who performs pest control by seed treatment or treatment during the growing seedling period.

European Patent Application Laid-Open No. 432600 (PTL1) discloses a plurality of compounds having the same ring structure as that of a compound represented by Formula (I), but the compounds are used as herbicides and there is no description about pest control.

Japanese Patent Application Laid-Open (JP-A) No. 5-78323 (PTL2) discloses the structural formula of N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound No. 3 in Table 1 of JP-A No. 5-78323), but fails to disclose a preparation method thereof and the compound is not included in a list of the group of compounds that are recognized to have pest control activity (Tables 2 and 3 of JP-A No. 5-78323).

European Patent Application Laid-Open No. 268915 (PTL3) discloses the structural formula of N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Example No. 12 in Table 7 of European Patent Application Laid-Open No. 268915), but fails to disclose a preparation method thereof and the Example does not include the compound as an example of the compounds having pest control activity.

Chemische Berichte (1955), 88, 1103-8 (NPL1) discloses a plurality of compounds having a ring structure similar to that of a compound represented by Formula (I) to be described below, but the compounds are disclosed only as synthetic intermediates.

European Patent Application Laid-Open No. 259738 (PTL4) discloses a plurality of compounds having a ring structure similar to that of a compound represented by Formula (I), but fails to disclose or suggest a compound having a trifluoroacetic acid imino structure.

Furthermore, these documents do not describe pest control activity when the novel iminopyridine derivative of the present invention is mixed with another pest control agent.

SUMMARY OF THE INVENTION

The present invention is contrived to provide a novel pest control agent to solve problems which chemicals in the related art have, such as reduction in drug sensitivity, long-term efficacy, safety during the use thereof and the like in the field of pest control.

In order to solve the problems, the present inventors have intensively studied, and as a result, have found that a novel iminopyridine derivative represented by Formula (I) has excellent pest control effects against pests and discovered a composition showing excellent pest control effects by containing these novel iminopyridine derivatives and at least one of other pest control agents, compared to when a single agent is used, and a use method thereof. The present invention is based on the finding.

Therefore, an object of the present invention is to provide a pest control composition prepared by containing at least one of a novel iminopyridine derivative represented by the following Formula (I) or acid addition salts thereof and at least one of other pest control agents, which is used in a low dose and shows excellent pest control effects against a wide range of pests.

(1) There is provided a pest control composition containing at least one of a novel iminopyridine derivative represented by the following Formula (I) or acid addition salts thereof as an active ingredient and at least one of other pest control agents:

[in the formula (I), Ar represents a phenyl group which may be substituted, a 5- to 6-membered heterocycle which may be substituted, or a 4- to 10-membered heterocycloalkyl group,

A represents a heterocycle having a 5- to 10-membered unsaturated bond including one or more nitrogen atoms, and has an imino group substituted with an R group at a position adjacent to the nitrogen atom present on the cycle,

Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, and

R represents any one of groups represented by the following Formulae (a) to (e), (y) or (z),

[here, R1 represents a hydrogen atom, a substituted C1 to C6 alkyl group, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, or a pentafluorophenyl group,

R2 represents a C1 to C6 alkyl group substituted with a halogen atom, an unsubstituted C3 to C6 branched or cyclic alkyl group, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted 5- to 10-membered heterocycle, or a substituted or unsubstituted benzyl group,

R3 represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group,

R4 represents a hydrogen atom, a formyl group, a C1 to C6 alkyl group which may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, a (C1 to C4) alkylthio (C2 to C5) alkynyl group, or a group represented by any of the following Formulae (f) to (n)

here, R4a, R4b and R4c represent a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle group, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group,

R4d represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle, and

R4e and R4f each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle,

R5 represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group,

R6 represents a hydrogen atom, a formyl group, a 0,0′-C1 to C4 alkyl phosphoryl group, a C1 to C18 alkyl group which may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, a (C1 to C4) alkylthio (C2 to C5) alkynyl group, or a group represented by any of the following Formulae (o) to (x)

here, R6a, R6b and R6c represent a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle group, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, and a (C1 to C4) alkylthio (C2 to C5) alkynyl group,

R6d represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle,

R6e and R6f each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, or a substituted or unsubstituted 5- to 10-membered heterocycle,

R6g and R6h each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, or a substituted or unsubstituted 5- to 10-membered heterocycle, and

R6i, R6j and R6k each independently represent a hydrogen atom, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, or a substituted or unsubstituted (C6 to C10) aryl group), and

R7 represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group,

Y1 and Y2 represent an oxygen atom or a sulfur atom, and may be the same or different, and

Ry represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, or a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group,

Rz represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group, and n represents 1 or 2],

(2) There is provided the pest control composition according to (1), containing at least one of an amine derivative represented by the following Formula (Ia) or acid addition salts thereof as an active ingredient and at least one of other pest control agents:

[here, Ar represents a pyridyl group which may be substituted with a halogen atom, a hydroxyl group, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, or a pyrimidyl group which may be substituted with a halogen atom, a C1 to C4 alkyl group which may be substituted with a halogen atom, an alkyloxy group which may be substituted with a halogen atom, a hydroxyl group, a cyano group, or a nitro group,

Y represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1 to C6 alkyl group which may be substituted with a halogen atom, a C1 to C6 alkyloxy group which may be substituted with a halogen atom, a cyano group, or a nitro group, and

R₁ represents a C1 to C6 alkyl group which is substituted with a halogen atom].

(3) There is provided the pest control composition according to (1), wherein Ar is a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, or a 2-chloro-5-pyrimidyl group.

(4) There is provided the pest control composition according to (1) or (3), wherein in Formula (I), A is the following Formula (A-1):

and Y is a hydrogen atom, a halogen atom, or a cyano group.

(5) There is provided the pest control composition according to (1), (3) to (4), wherein R in Formula (I) is a group with Formula (c).

(6) There is provided the pest control composition according to (1), (3) to (4), wherein R in Formula (I) is a group with Formula (a).

(7) There is provided the pest control composition according to (1), (3) to (4), wherein R in Formula (I) is a group with Formula (d)

and R4 is a C1 to C18 alkyl group which may be substituted, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group, a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group, a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group, a (C1 to C4) alkoxy (C2 to C5) alkynyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group, or a (C1 to C4) alkylthio (C2 to C5) alkynyl group, and

R5 is a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, and R5 is a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, or a C2 to C6 alkynyl group which may be substituted with a halogen atom.

(8) There is provided the pest control composition according to (1), wherein the iminopyridine derivative is N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide, N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide, or N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide.

(9) There is provided a method for protecting useful plants or animals from pests, including: treating pests, useful plants, seeds of useful plants, soil, cultivation carriers or animals as a target with an effective amount of the pest control composition.

(10) There is provided a combination (combined product) including the iminopyridine derivative represented by Formula (I) and at least one of other pest control agents.

(11) There is provided a use of the pest control composition for protecting useful plants or animals from pests.

It is possible to effectively perform pest control against cabbage moths, Spodoptera litura, aphids, planthoppers, leafhoppers, thrips and other numerous pests by using novel iminopyridine derivative of the present invention.

BRIEF DESCRIPTION OF THE DRAWINGS

A novel iminopyridine derivative represented by Formula (I) may be prepared by the following method.

(I-1) may be obtained by reacting a compound represented by the following Formula (II-1) with a compound represented by ArCH2X [the definition of Ar, A, Y and R1 has the same meaning as the definition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide, and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine, as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at 0° C. to 200° C., and it is preferred that reagents are added at 20° C. to 40° C. and the reaction is performed at 60° C. to 80° C.

The compound represented by Formula (II-1) may be obtained by reacting a compound represented by R1-C(═O)X, R1-C(═O)OC(═O)R1, R1C(═O)OR′ [X represents a halogen atom or OTs, OMs and the like, R′ represents a C1 to C6 alkyl group, and the definition of R1, A and Y has the same meaning as the definition described above] and the like with a compound represented by the following Formula (III) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C. The compound represented by Formula (II-1) may be obtained by reacting the compound represented by Formula (III) with a carboxylic acid represented by R1-COOH [the definition of R1 has the same meaning as the definition described above]using a dehydration condensation agent in the presence or absence of a base, or may be obtained by performing the reaction using phosphorus pentaoxide, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride and oxalyl dichloride in the absence of a base.

It is possible to use a carbodiimide-based compound such as dicyclohexylcarbodiimide and 1-ethyl-3-(3-[dimethylaminopropyl])carbodiimide hydrochloride as the dehydration condensation agent.

When the reaction is performed in the presence of a base, it is possible to use, for example, a carbonate such as potassium carbonate or sodium carbonate, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine, as the base.

The reaction is preferably performed by using a solvent, and it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C. The compound represented by Formula (I-1) may be obtained by reacting a compound represented by R1-C(═O)X, R1-C(═O)OC(═O)R1, R1C(═O)OR′ [X represents a halogen atom or OTs, OMs and the like, R′ represents a C1 to C6 alkyl group, and the definition of Ar, A, Y and R1 has the same meaning as the definition described above] and the like with a compound represented by the following Formula (IV) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C. The compound represented by Formula (I-1) may be obtained by reacting the above-described compound represented by Formula (IV) with a carboxylic acid represented by R1-COOH [the definition of R1 has the same meaning as the definition described above] using a dehydration condensation agent in the presence or absence of a base, or may be obtained by performing the reaction using phosphorus pentaoxide, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride and oxalyl dichloride in the absence of a base.

It is possible to use a carbodiimide-based compound such as dicyclohexylcarbodiimide and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride as the dehydration condensation agent.

When the reaction is performed in the presence of a base, it is possible to use, for example, a carbonate such as potassium carbonate or sodium carbonate, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine, as the base.

The reaction is preferably performed by using a solvent, and it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C. The compound represented by Formula (IV) may be obtained by reacting the above-described compound represented by Formula (III) with a compound represented by ArCH2X [the definition of Ar and X has the same meaning as the definition described above] in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine, as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but N,N-dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.

When Formula (I-1) is synthesized via Formula (II-1) from the compound represented by Formula (III), or when Formula (I-1) is synthesized via Formula (IV) from the compound represented by Formula (III), the reaction may be continuously performed without taking out Formula (II-1) or Formula (IV), or the reactions from Formula (III) to Formula (I-1) may be simultaneously performed in the same vessel.

The compound represented by Formula (I-2) may be obtained by reacting a compound represented by the following Formula (I-2a) with a compound represented by ArCH2X [the definition of Ar, A, Y and R2 has the same meaning as the definition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine, as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at 0° C. to 200° C., and it is preferred that reagents are added at 20° C. to 40° C. and the reaction is performed at 60° C. to 80° C.

The compound represented by Formula (I-2a) may be obtained by reacting the above-described compound represented by Formula (III) with a compound represented by R2OC(═O)X (the definition of R2 and X has the same meaning as the definition described above] or represented by the following Formula (I-2b) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether, and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but acetonitrile, dichloromethane or the like is preferably used.

The reaction may be performed usually at 0° C. to 200° C., and is performed preferably at 20° C. to 80° C.

The compound represented by Formula (I-2) may be obtained by reacting the above-described compound represented by Formula (IV) with a compound represented by R2OC(═O)X (the definition of R2 and X has the same meaning as the definition described above] or represented by the above-described Formula (I-2b) in the presence or absence of a base. When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but acetonitrile, dichloromethane or the like is preferably used.

The reaction may be performed usually at 0° C. to 200° C., and is performed preferably at 20° C. to 80° C.

The compound represented by Formula (I-3) may be synthesized by acting a sulfurizing reagent on a compound (the definition of Ar, A, Y and R3 has the same meaning as the definition described above) represented by the following Formula (II-3a), which may be synthesized in the same manner as described in Formula (I-1), in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base, but potassium carbonate, sodium carbonate or the like is preferably used.

As the sulfurizing reagent, phosphorus pentasulfide, Lawesson's reagent, hydrogen sulfide and the like may be used.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but toluene, tetrahydrofuran or the like is preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C. The compound represented by Formula (I-3) may be obtained by reacting a compound represented by the following Formula (II-3b) with a compound represented by ArCH2X [the definition of Ar, A, Y and R3 has the same meaning as the definition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at 0° C. to 200° C., and it is preferred that reagents are added at 20° C. to 40° C. and the reaction is performed at 60° C. to 80° C.

The compound represented by Formula (II-3b) may be synthesized by acting a sulfurizing reagent on a compound (the definition of A, Y and R3 has the same meaning as the definition described above) represented by Formula (II-3c), which may be synthesized in the same manner as described in Formula (II-1), in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base, but potassium carbonate, sodium carbonate or the like is preferably used.

As the sulfurizing reagent, phosphorus pentasulfide, Lawesson's reagent, hydrogen sulfide and the like may be used. The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but toluene, tetrahydrofuran and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.

The compound represented by Formula (I-4) may be obtained by reacting a compound represented by the following Formula (II-4a), which may be synthesized in the same manner as described in Formula (I-3) with a compound represented by R4-NH2 (the definition of Ar, A, Y, R4 and R5 has the same meaning as the definition described above).

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but alcohols such as methanol and ethanol are preferably used.

The reaction, if performed in the presence of silver carbonate, copper carbonate and the like, progresses quickly, but may proceed without the compound.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.

The compound represented by Formula (I-4) may be obtained by reacting a compound represented by the following Formula (I-4b) or a salt thereof with R4-X, R4-O—R4 and R4-OR′ (the definition of R4, R′, Ar, A, Y and R5 has the same meaning as the definition described above, and X represents a halogen atom) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water either alone or in combination of two or more thereof, but toluene, dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C. The compound represented by Formula (I-4b) may be obtained by reacting a compound represented by Formula (II-4a) with ammonia or an alcohol solution thereof, ammonium chloride and the like.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but alcohols such as methanol and ethanol are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C.

The compound represented by Formula (I-5) may be obtained by reacting a compound represented by the following Formula (II-5b) with R6-X (the definition of AR, A, Y, R6 and R7 has the same meaning as the definition described above, and X represents a halogen atom), R6-O—R6 or R6-OR′ (the definition of R′ has the same meaning as the definition described above) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers, dichloromethane and chloroform are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C.

When R6 represents —C(═O)R6a (R6a has the same meaning as described above), the compound represented by Formula (I-5) may be obtained by reacting the compound represented by Formula (II-5b) with a carboxylic acid represented by R6a-C(═O)OH (the definition of R6a has the same meaning as the definition described above) using a dehydration condensation agent in the presence or absence of a base, or may be obtained by performing the reaction using phosphorus pentaoxide, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride and oxalyl dichloride in the absence of a base.

It is possible to use a carbodiimide-based compound such as dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and the like as the dehydration condensation agent.

When the reaction is performed in the presence of a base, it is possible to use, for example, a carbonate such as potassium carbonate or sodium carbonate, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.

The reaction is preferably performed by using a solvent, and it is possible to use, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 50° C.

When R6 represents CONR6eR6f (the definition of R6e and R6f has the same meaning as the definition described above, and R6e or R6f represents a hydrogen atom) or CSNR6gR6h (the definition of R6g and R6h has the same meaning as the definition described above, and R6g or R6h represents a hydrogen atom), the compound of Formula (I-5) may be obtained by reacting the Formula (II-5b) with a compound represented by R″N═C═O (R″ represents a C1 to C6 alkyl group which may be substituted with a halogen atom, a C2 to C6 alkenyl group which may be substituted with a halogen atom, a C2 to C6 alkynyl group which may be substituted with a halogen atom, a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C1 to C5) alkyl group, a substituted or unsubstituted (C6 to C10) aryl group, and a substituted or unsubstituted 5- to 10-membered heterocycle) in the presence or absence of a base. When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base. The reaction is preferably performed by using a solvent, and it is possible to use, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but nitriles such as acetonitrile are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.

When R6 represents CONR6eR6f (the definition of R6e and R6f has the same meaning as the definition described above), the compound of Formula (I-5) may be obtained by reacting the above-described compound represented by Formula (II-5b) with a compound represented by the following Formula (II-5c) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.

The reaction is preferably performed by using a solvent, and it is possible to use, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but nitriles such as acetonitrile are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.

The compound represented by Formula (II-5b) may be obtained by reacting the compound (the definition of Ar, A, Y and R7 has the same meaning as the definition described above) represented by Formula (II-5a), which may be synthesized in the same manner as described in Formula (I-3) with hydroxylamine or a salt thereof in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but toluene, N,N-dimethylformamide, acetonitrile, ethers, dichloromethane, chloroform and the like are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.

The compound represented by Formula (I-5) may also be obtained by reacting the compound represented by Formula (II-5a) with a compound represented by R6-ONH2 or a salt thereof in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride, a carbonate such as potassium carbonate or sodium carbonate, an alkali metal hydroxide such as potassium hydroxide and sodium hydroxide, tertiary amines such as triethylamine and 1,8-diazabicyclo[4.3.0]non-5-ene, and unsubstituted or substituent-containing pyridines, such as pyridine and 4-dimethylaminopyridine as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction. When a solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol and propanol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, and water, either alone or in combination of two or more thereof, but alcohols such as methanol and ethanol are preferably used.

The reaction may be performed usually at −80° C. to 100° C., and is performed preferably in a range from 20° C. to 80° C.

The reaction, if performed in the presence of silver carbonate, copper carbonate and the like, progresses quickly, but may proceed without the compound.

The compound represented by Formula (I-6) [the definition of Ar, A, Y, Y1, Y2, and Ry has the same meaning as the definition described above] may be obtained by reacting according to Phosphorus, sulfur, and silicon and the related elements (2006) 181, 2337-2344.

The compound represented by Formula (I-7) [the definition of Ar, A, Y, Ry and n has the same meaning as the definition described above] may be obtained by reacting a compound represented by the following Formula (II-7a) with a compound represented by ArCH2X [the definition of Ar has the same meaning as the definition described above, and X represents a halogen atom or OTs, OMs and the like] in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride and the like, a carbonate such as potassium carbonate or sodium carbonate and the like, an alkali metal hydroxide such as potassium hydroxide, sodium hydroxide and the like, tertiary amines such as triethylamine, 1,8-diazabicyclo[4.3.0]non-5-ene and the like, and unsubstituted or substituent-containing pyridines, such as pyridine, 4-dimethylaminopyridine and the like, as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when the solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used. The reaction may be performed usually at from 0° C. to 200° C., and it is preferred that reagents are added at from 20° C. to 40° C. and the reaction is performed at from 60° C. to 80° C.

The compound represented by Formula (II-7a) may be obtained by reacting a compound represented by (II-7b) [X represents a halogen atom, and the definition of Rz and n has the same meaning as the definition described above] with a compound represented by in the following Formula (III) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride and the like, a carbonate such as potassium carbonate or sodium carbonate and the like, an alkali metal hydroxide such as potassium hydroxide, sodium hydroxide and the like, tertiary amines such as triethylamine, 1,8-diazabicyclo[4.3.0]non-5-ene and the like, and unsubstituted or substituent-containing pyridines, such as pyridine, 4-dimethylaminopyridine and the like, as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when the solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at from 0° C. to 200° C., and it is preferred that reagents are added at from 20° C. to 40° C. and the reaction is performed at from 60° C. to 80° C.

The compound represented by Formula (I-7) may be obtained by reacting a compound represented by (II-7b) [X represents a halogen atom, and the definition of Rz has the same meaning as the definition described above] with a compound represented by in the following Formula (IV) in the presence or absence of a base.

When the reaction is performed in the presence of a base, it is possible to use, for example, an alkali metal hydride such as sodium hydride and the like, a carbonate such as potassium carbonate or sodium carbonate and the like, an alkali metal hydroxide such as potassium hydroxide, sodium hydroxide and the like, tertiary amines such as triethylamine, 1,8-diazabicyclo[4.3.0]non-5-ene and the like, and unsubstituted or substituent-containing pyridines, such as pyridine, 4-dimethylaminopyridine and the like, as the base.

The reaction may be performed without a solvent or using a solvent which does not affect the reaction, and when the solvent is used, it is possible to use solvents such as, for example, amides such as N,N-dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, sulfoxides such as dimethyl sulfoxide, ethers such as diethyl ether and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatic hydrocarbons such as benzene, xylene and toluene, alcohols such as methanol, ethanol, propanol and isopropyl alcohol, ketones such as acetone and methyl ethyl ketone, aliphatic hydrocarbons such as hexane, heptane and octane, and halogen hydrocarbons such as dichloromethane, chloroform, chlorobenzene and dichlorobenzene, either alone or in combination of two or more thereof, but N,N-dimethylformamide and the like are preferably used.

The reaction may be performed usually at from 0° C. to 200° C., and it is preferred that the reaction is performed at from 0° C. to 80° C.

Examples of a substituent that may be substituted of “a phenyl group which may be substituted” and “a 5- to 6-membered heterocycle which may be substituted”, which are represented by Ar, include a halogen atom, a C1 to C4 alkyl group which may be substituted with a halogen atom, a C1 to C4 alkyloxy group which may be substituted with a halogen atom, a hydroxyl group, a cyano group, a nitro group and the like, preferably a halogen atom, a trifluoromethyl group and a cyano group, and particularly preferably a halogen atom.

Specific examples of the “a phenyl group which may be substituted” represented by Ar of a nitrogen-containing heterocyclic derivative compound having a 2-imino group represented by Formula (I) include a phenyl group and a 3-cyano phenyl group.

“A 5- to 6-membered heterocycle which may be substituted”, represented by Ar of a nitrogen-containing heterocyclic derivative compound having a 2-imino group represented by Formula (I) represents an aromatic 5- to 6-membered heterocycle including one or two of a heteroatom such as an oxygen atom, a sulfur atom or a nitrogen atom, specific examples thereof include a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a thiazole ring, an oxazole ring and the like, and preferable aspects thereof include a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-trifluoromethyl-3-pyridyl group, a 6-chloro-3-pyridazinyl group, a 5-chloro-2-pyrazinyl group, a 2-chloro-5-pyrimidinyl group, a 2-chloro-5-thiazolyl group, a 2-chloro-4-pyridyl group, and more preferably a 6-chloro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidinyl group.

Specific examples of “a 4- to 10-membered heterocycloalkyl group” represented by Ar of a nitrogen-containing hetero ring derivative having a 2-imino group represented by Formula (I) include a 2-tetrahydrofuranyl group, a 3-tetrahydrofuranyl group and the like and preferably a 3-tetrahydrofuranyl group. “A heterocycle having a 5- to 10-membered unsaturated bond including one or more nitrogen atoms”, which A of a nitrogen-containing heterocyclic derivative having a 2-imino group represented by Formula (I) represents, means that

in Formula (I) represents any one ring represented by each of the following Formulae A-1 to A-40. In each formula, the end of a double bond is the substitution position of a nitrogen atom.

The ring is preferably the ring of Formulae A-1, A-13, A-14, A-15, A-16, A-23, A-25, A-38 and A-39 and more preferably the ring of Formula A-1.

“A C1 to C6 alkyl group which may be substituted with a halogen atom”, which Y represents, is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of halogen atoms which may be substituted is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more.

Specific examples of “a C1 to C6 alkyloxy group which may be substituted with a halogen atom” which Y represents include a methoxy group, an ethoxy group, a trifluoromethyloxy group and a difluoromethyloxy group.

A preferred aspect of Y is preferably a hydrogen atom or a halogen atom and more preferably a hydrogen atom.

A preferred aspect of R is a group represented by the Formula (a), (c) and (d) described above.

in Formula (I), “a substituted C1 to C6 alkyl group” which R1 represents is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted substituents is the number of hydrogen atoms which the alkyl group has. Examples of the substituted substituent include a halogen atom, a hydroxyl group, a cyano group, a nitro group, a phenyl group (this phenyl group may be substituted with a C1 to C4 alkyl group which may be substituted with a halogen, a C1 to C4 alkyloxy group which may be substituted with a halogen, a hydroxyl group, or a halogen atom), a phenoxy group (this phenyl group may be substituted with a C1 to C4 alkyl group which may be substituted with a halogen, a C1 to C4 alkyloxy group which may be substituted with a halogen, a hydroxyl group, or a halogen atom), a benzyloxy group (the phenyl group in this benzyloxy group may be substituted with a C1 to C4 alkyl group which may be substituted with a halogen, a C1 to C4 alkyloxy group which may be substituted with a halogen, a hydroxyl group, or a halogen atom), and the like. Specific examples thereof include a 1,1,1-trifluoroethyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a 2-cyanoethyl group, a 2-nitroethyl group and the like. A 1,1,1-trifluoroethyl group, a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group are preferred, a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group are more preferred, and a trifluoromethyl group are particularly preferred.

In Formula (I), “a C1 to C6 alkyl group which may be substituted with a halogen atom” which R3, R5, R7, Ry, and Rz represent is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a trifluoroisopropyl group, and a hexafluoroisopropyl group, and the like.

R3 is each preferably an ethyl group, an isopropyl group, a cyclopropyl group, a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group, more preferably a trifluoromethyl group, a difluorochloromethyl group, a difluoromethyl group and a pentafluoroethyl group, and particularly preferably a trifluoromethyl group. R5 is preferably a trifluoromethyl group, a trichloromethyl group, a dichloromethyl group, a difluoromethyl group, a difluorochloromethyl group, a chloromethyl group and a pentafluoroethyl group, more preferably a trifluoromethyl group, a difluoromethyl group, a difluorochloromethyl group and a pentafluoroethyl group, and particularly preferably a trifluoromethyl group. R7 is preferably a trifluoromethyl group, a trichloromethyl group, a dichloromethyl group, a difluoromethyl group, a difluorochloromethyl group, a chloromethyl group and a pentafluoroethyl group, more preferably a trifluoromethyl group, a difluoromethyl group, a difluorochloromethyl group and a pentafluoroethyl group, and particularly preferably a trifluoromethyl group.

Ry is preferably a methyl group, ethyl group, propyl group or isopropyl group. Rz is preferably a methyl group or trifluoromethyl group.

“A C1 to C6 alkyl group which may be substituted with a halogen atom”, which R2 represents, is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a 1-(trifluoromethyl)ethyl group, a 1-trifluoromethyl-2,2,2-trifluoroethyl group, a pentafluoroethyl group, and a difluorocyclopropyl group, and the like, and preferred examples thereof include a 2,2,2-trifluoroethyl group, a 1-(trifluoromethyl)ethyl group and a 1-trifluoromethyl-2,2,2-trifluoroethyl group.

“A C1 to C6 alkyl group which may be substituted” which R4 and R6 represent is an alkyl group having 1 to 18 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituents which may be substituted is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more. Examples of the substituent which may be substituted include a halogen atom, a hydroxyl group, a cyano group, a nitro group and the like. Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an s-butyl group, a t-butyl group, a 3-methyl-2-butyl group, a 3-pentyl group, a 4-heptyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an n-octyl group, an n-tridecyl group, an n-hexadecyl group, an n-octadecyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group, a 2-hydroxyethyl group, a 2-hydroxy-n-propyl group, a 3-hydroxy-n-propyl group, a 2,3-dihydroxy-n-propyl group, a cyanomethyl group, a 2-cyanoethyl group, a 2-nitroethyl group and the like.

R4 is each preferably a methyl group, an ethyl group, a 2,2,2-trifluoroethyl group, a 2,2-difluoroethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, a t-butyl group, a cyclopentyl group, a cyclohexyl group and a 2-hydroxyethyl group, and more preferably a methyl group, an ethyl group and a cyclopropyl group. R6 is preferably a methyl group, an ethyl group, an isopropyl group a cyclopropyl group, a t-butyl group and a cyanomethyl group, and more preferably a methyl group, an ethyl group, a cyclopropyl group and a t-butyl group.

“A C1 to C6 alkyl group which may be substituted with a halogen atom”, which R4a, R4b, R4c, R4d, R4e, R4f, R6a, R6b, R6c, R6d, R6e, R6f, R6g, R6h, R6i, R6j and R6k represent, is an alkyl group having 1 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkyl group has. When a branched or cyclic alkyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a trifluoromethyl group, a trichloromethyl group, a difluorochloromethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a chloromethyl group, a difluoroethyl group, a 2-chloroethyl group, a dichloroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a difluorocyclopropyl group and the like. R6a is preferably a methyl group, an ethyl group, an isopropyl group and a cyclopropyl group. R6b is preferably a methyl group.

“A C2 to C6 alkenyl group which may be substituted with a halogen atom”, which R1, R2, R3, R4, R4a, R4b, R4c, R4d, R4e, R4f, R5, R6, R6a, R6b, R6c, R6d, R6e, R6f, R6g, R6h, R6i, R6j, R6k, R7, Ry and Rz represent, is an alkenyl group having 2 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkenyl group has. When a branched or cyclic alkenyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include an ethenyl group, a 1-propenyl group, a 2-propenyl group, a 2-fluoro-1-propenyl group, a 2-methyl-1-propenyl group and the like, and preferred examples thereof include an ethenyl group.

“A C2 to C6 alkynyl group which may be substituted with a halogen atom”, which R1, R2, R3, R4, R4a, R4b, R4c, R4d, R4e, R4f, R5, R6, R6a, R6b, R6c, R6d, R6e, R6f, R6g, R6h, R6i, R6j, R6k, R7, Ry and Rz represent, is an alkynyl group having 2 to 6 carbon atoms, which is chained, branched, cyclic or combination thereof, and the upper limit of the number of substituted halogen atoms is the number of hydrogen atoms which the alkynyl group has. When a branched or cyclic alkynyl group is included, it is obvious that the number of carbons is 3 or more. Specific examples thereof include a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group and the like, and preferred examples thereof include a 1-propynyl group, a 2-propynyl group and a 2-butynyl group.

The (C6 to C10) aryl of “a substituted or unsubstituted (C6 to C10) aryl group, a substituted or unsubstituted (C6 to C10) aryl (C1 to C6) alkyl group, a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkenyl group and a substituted or unsubstituted (C6 to C10) aryl (C2 to C6) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R7, Ry and Rz represent, specifically represents a phenyl group and a naphthyl group, and the (C1 to C6) alkyl group, the (C2 to C6) alkenyl group and the (C2 to C6) alkynyl group may have a straight chain, branch or ring. Examples of the substituent which may be substituted with an aryl group include a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Specific examples thereof include a phenyl group, a benzyl group, a 2-phenylethyl group, a 2-phenylethenyl group, a 2-phenylethynyl group, a 4-methylphenyl group, a 2-cyanophenyl group, a 3-chlorophenyl group, a 4-methoxyphenyl group, a 3-cyanophenyl group, 1,1-diphenylmethyl group, a naphthylethyl group, a naphthylpropyl group and the like, and preferred examples thereof include a benzyl group and a 2-phenylethyl group, a naphthylethyl group, a naphthylpropyl group.

The (C1 to C6) alkyl group, (C2 to C6) alkenyl group and (C2 to C6) alkenyl group of “a substituted or unsubstituted phenoxy (C1 to C6) alkyl group, a substituted or unsubstituted phenoxy (C2 to C6) alkenyl group and a substituted or unsubstituted phenoxy (C2 to C6) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R7, Ry and Rz represent, may have a straight chain, branch or ring. Examples of the substituent which may be substituted with a phenoxy group include a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Specific examples thereof include a phenoxy group, a phenoxymethyl group, a 2-phenoxyethyl group, a 2-phenoxyethenyl group, a 2-phenoxyethynyl group, a 4-chlorophenoxy group, a 2-methylphenoxy group and the like, and preferred examples thereof include a 2-phenoxyethyl group.

The 5- to 10-membered heterocycle of “a substituted or unsubstituted 5- to 10-membered heterocycle, a substituted or unsubstituted 5- to 10-membered heterocycle (C1 to C6) alkyl group, a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkenyl group and a substituted or unsubstituted 5- to 10-membered heterocycle (C2 to C6) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R7, Ry and Rz represent, represents a ring including a hetero atom, such as an oxygen atom, a sulfur atom or a nitrogen atom as an atom constituting 1 to 4 rings, and examples thereof include a furanyl group, a thienyl group, a pyridyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a pyrimidinyl group, a morpholinyl group, a triazolyl group, an imidazolyl group, a triazolyl group, a tetrahydrofuranyl group, a quinolinyl group and the like. Examples of the substituent which may be substituted with a heterocycle include a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. The (C1 to C6) alkyl group, (C2 to C6) alkenyl group and (C2 to C6) alkenyl group may have a straight chain, branch or ring. Specific examples thereof include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-pyridylmethyl group, a 3-pyridylmethyl group, a 4-pyridylmethyl group, a 2-(4-pyridyl)ethenyl group, a 2-(4-pyridyl)ethynyl group, a 2-furanylmethyl group, a 2-thienylmethyl group, a 2-tetrahydrofuranylmethyl group and the like, and preferred examples thereof include a 2-pyridylmethyl group, a 3-pyridylmethyl group, a 4-pyridylmethyl group, a 2-furanylmethyl group, a 2-thienylmethyl group and a 2-tetrahydrofuranylmethyl group.

The (C1 to C4) alkoxy of “a (C1 to C4) alkoxy (C1 to C5) alkyl group, a (C1 to C4) alkoxy (C2 to C5) alkenyl group and a (C1 to C4) alkoxy (C2 to C5) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R6e, R6f, R7 and Rz represent, represents a (C1 to C4) alkyloxy, alkenyloxy and alkynyloxy having a straight chain, branch or ring. Specific examples thereof include a methoxymethyl group, a 2-methoxyethyl group, an ethoxymethyl group, a 2-ethoxyethyl group, a 3-methoxy-2-propenyl group, a 3-methoxy-2-propynyl group and the like. R4 is preferably a 2-methoxyethyl group.

The (C1 to C4) alkylthio of “a (C1 to C4) alkylthio (C1 to C5) alkyl group, a (C1 to C4) alkylthio (C2 to C5) alkenyl group and a (C1 to C4) alkylthio (C2 to C5) alkynyl group”, which R3, R4, R4a, R4b, R4c, R5, R6, R6a, R6b, R6c, R6e, R6f, R7 and Rz represent, represents a (C1 to C4) alkylthio, alkenylthio and alkynylthio having a straight chain, branch or ring. Examples thereof include a methylthiomethyl group, a 2-methylthioethyl group, an ethylthiomethyl group, a 2-ethylthioethyl group, a 3-methylthio-2-propenyl group, a 3-methylthio-2-propynyl group and the like. R4 is preferably a 2-methylthioethyl group.

The (C6 to C10) aryl of “a substituted or unsubstituted (C6 to C10) aryl group”, which R2, R4d, R4e, R4f, R6d, R6e, R6f, R6g, R6h, R6i, R6j and R6k represent, specifically represents a phenyl group and a naphthyl group, and the (C1 to C6) alkyl group, (C2 to C6) alkenyl group and (C2 to C6) alkenyl group may have a straight chain, branch or ring. Examples of the substituent which may be substituted with an aryl group include a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Specific examples thereof include a phenyl group, a 2-methylphenyl group, a 3-methoxyphenyl group, a 4-nitrophenyl group, a 4-cyanophenyl group and the like.

The 5- to 10-membered heterocycle of “a substituted or unsubstituted 5- to 10-membered heterocycle”, which R2, R4d, R4e, R4f, R6d, R6e, R6f, R6g and R6h represent, represents a ring including a hetero atom, such as an oxygen atom, a sulfur atom or a nitrogen atom as an atom constituting 1 to 4 rings, and examples thereof include a furanyl group, a thienyl group, a pyridyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a pyrimidinyl group, a morpholinyl group, a triazolyl group, an imidazolyl group, a triazolyl group, a tetrahydrofuranyl group, a quinolinyl group and the like. Examples of the substituent which may be substituted with a heterocycle include a halogen atom, a C1 to C4 alkyl group which may be substituted with halogen, a C1 to C4 alkyloxy group which may be substituted with halogen, a C3 to C6 cyclic alkyl group, a methylsulfonyl group, a methoxy group, a nitro group, a cyano group and the like. Specific examples thereof include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-furanyl group, a 2-thienyl group, a 2-tetrahydrofuranyl group and the like.

As a preferred aspect of a compound represented by Formula (I),

R represents the following Formula (a),

Ar represents a 6-chloro-3-pyridyl group, a 2-chloro-5-thiazolyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, a 2-chloro-5-pyrimidinyl group, a 6-trifluoromethyl-3-pyridyl group and a 2-chloro-5-pyrimidinyl group,

A represents a ring represented by A-1, A-13, A-14, A-15, A-16, A-23 and A-38,

Y represents a hydrogen atom and a 3-cyano group, and

R1 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group, a pentafluoroethyl group, a trifluoroethyl group, an ethenyl group and a 2-propynyl group.

As another preferred aspect of a compound represented by Formula (I),

R represents the following Formula (c),

Ar represents a 6-chloro-3-pyridyl group, a 2-chloro-5-thiazolyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group, a 2-chloro-5-pyrimidyl group and a 6-trifluoromethyl-3-pyridyl group,

A represents a ring represented by A-1,

Y represents a hydrogen atom, and

R3 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group.

As still another preferred aspect of a compound represented by Formula (I),

R represents the following Formula (d),

Ar represents a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidyl group,

A represents a ring represented by A-1,

Y represents a hydrogen atom,

R4 represents a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a cyclopropyl group, a cyclobutyl group, a cyclohexyl group, and cyclopentyl group, and

R5 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group.

As yet another preferred aspect of a compound represented by Formula (I),

R represents the following Formula (e) group

Ar represents a 6-chloro-3-pyridyl group, a 6-chloro-5-fluoro-3-pyridyl group, a 6-fluoro-3-pyridyl group, a 6-bromo-3-pyridyl group and a 2-chloro-5-pyrimidyl group,

A represents a ring represented by A-1,

Y represents a hydrogen atom, and

R6 represents a hydrogen atom, a methyl group, an ethyl group, a 2-propenyl group, a methylcarbonyl group, an ethylcarbonyl group, a cyclopropylcarbonyl group, an ethenylcarbonyl group, a 2-propynylcarbonyl group, a benzoyl group, a 3-pyridylcarbonyl group, a methyloxycarbonyl group and a phenyloxycarbonyl group, and

R7 represents a trifluoromethyl group, a difluoromethyl group, a chlorodifluoromethyl group and a pentafluoroethyl group.

Specific examples of the compound of Formula (I) include a compound represented by a combination of the following Table A and Table B.

TABLE 1 Table A Compound No. Ar A Y R Table 1- 6-Chloro-3-pyridyl A-1 H represents a 1 5~1- combination of 710 substituents corresponding to each row of Nos. (1 and 6) below of Table B Table 2- 2-Chloro-5-thiazolyl A-1 H represents a 2 1~2- combination of 710 substituents corresponding to each row of Table B Table 3- 6-Fluoro-3-pyridyl A-1 H represents a 3 2~3- combination of 710 substituents corresponding to each row of Nos. (1 and 3) below of Table B Table 4- 6-Bromo-3-pyridyl A-1 H represents a 4 2~4- combination of 710 substituents corresponding to each row of Nos. (1 and 3) below of Table B Table 5- 6-Chloro-5-fluoro- A-1 H represents a 5 2~5- 3-pyridyl combination of 710 substituents corresponding to each row of Nos. (1 and 3) below of Table B Table 6- 2-Chloro-5- A-1 H represents a 6 2~6- pyrimidinyl combination of 710 substituents corresponding to each row of Nos. (1 and 3) below of Table B Table 7- 5-Chloropyrazin- A-1 H represents a 7 1~7- 2-yl combination of 710 substituents corresponding to each row of Table B Table 8- 6-Chloropyridazin- A-1 H represents a 8 1~8- 3-yl combination of 710 substituents corresponding to each row of Table B Table 9- 2-Chloro-5-oxazolyl A-1 H represents a 9 1~9- combination of 710 substituents corresponding to each row of Table B Table 10- 6-trifluoromethyl- A-1 H represents a 10 1~10- 3-pyridyl combination of 710 substituents corresponding to each row of Table B Table 11- 3-tetrahydrofuranyl A-1 H represents a 11 1~11- combination of 710 substituents corresponding to each row of Table B Table 12- 2-Chloro-4-pyridyl A-1 H represents a 12 1~12- combination of 710 substituents corresponding to each row of Table B Table 13- 3-Cyanophenyl A-1 H represents a 13 1~13- combination of 710 substituents corresponding to each row of Table B Table 14- 6-Chloro-3-pyridyl A-1 3-F represents a 14 1~14- combination of 710 substituents corresponding to each row of Table B Table 15- 2-Chloro-5-thiazolyl A-1 3-F represents a 15 1~15- combination of 710 substituents corresponding to each row of Table B Table 16- 6-Fluoro-3-pyridyI A-1 3-F represents a 16 1~16- combination of 710 substituents corresponding to each row of Table B Table 17- 6-Bromo-3-pyridyl A-1 3-F represents a 17 1~17- combination of 710 substituents corresponding to each row of Table B Table 18- 6-Chloro-5-fluoro- A-1 3-F represents a 18 1~18- 3-pyridyl combination of 710 substituents corresponding to each row of Table B Table 19- 2-Chloro-5- A-1 3-F represents a 19 1~19- pyrimidinyl combination of 710 substituents corresponding to each row of Table B Table 20- 5-Chloropyrazin- A-1 3-F represents a 20 1~20- 2-yl combination of 710 substituents corresponding to each row of Table B Table 21- 6-Chloropyridazin- A-1 3-F represents a 21 1~21- 3-yl combination of 710 substituents corresponding to each row of Table B Table 22- 2-Chloro-5-oxazolyl A-1 3-F represents a 22 1~22- combination of 710 substituents corresponding to each row of Table B Table 23- 6-trifluoromethyl- A-1 3-F represents a 23 1~23- 3-pyridyl combination of 710 substituents corresponding to each row of Table B Table 24- 3-tetrahydrofuranyl A-1 3-F represents a 24 1~24- combination of 710 substituents corresponding to each row of Table B Table 25- 6-Chloro-3-pyridyl A-1 4-F represents a 25 1~25- combination of 710 substituents corresponding to each row of Table B Table 26- 2-Chloro-5-thiazolyl A-1 4-F represents a 26 1~26- combination of 710 substituents corresponding to each row of Table B Table 27- 6-Fluoro-3-pyridyl A-1 4-F represents a 27 1~27- combination of 710 substituents corresponding to each row of Table B Table 28- 6-Bromo-3-pyridyl A-1 4-F represents a 28 1~28- combination of 710 substituents corresponding to each row of Table B Table 29- 6-Chloro-5-fluoro- A-1 4-F represents a 29 1~29- 3-pyridyl combination of 710 substituents corresponding to each row of Table B Table 30- 2-Chloro-5- A-1 4-F represents a 30 1~30- pyrimidinyl combination of 710 substituents corresponding to each row of Table B Table 31- 5-Chloropyrazin- A-1 4-F represents a 31 1~31- 2-yl combination of 710 substituents corresponding to each row of Table B Table 32- 6-Chloropyridazin- A-1 4-F represents a 32 1~32- 3-yl combination of 710 substituents corresponding to each row of Table B

TABLE 2 Table A Compound No. Ar A Y R Table 33- 2-Chloro-5-oxazolyl A-1 4-F represents a 33 1~33- combination of 710 substituents corresponding to each row of Table B Table 34- 6-trifluoromethyl- A-1 4-F represents a 34 1~34- 3-pyridyl combination of 710 substituents corresponding to each row of Table B Table 35- 3-tetrahydrofuranyl A-1 4-F represents a 35 1~35- combination of 710 substituents corresponding to each row of Table B Table 36- 6-Chloro-3-pyridyl A-1 5-F represents a 36 1~36- combination of 710 substituents corresponding to each row of Table B Table 37- 2-Chloro-5-thiazolyl A-1 5-F represents a 37 1~37- combination of 710 substituents corresponding to each row of Table B Table 38- 6-Fluoro-3-pyridyl A-1 5-F represents a 38 1~38- combination of 710 substituents corresponding to each row of Table B Table 39- 6-Bromo-3-pyridyl A-1 5-F represents a 39 1~39- combination of 710 substituents corresponding to each row of Table B Table 40- 6-Chloro-5-fluoro- A-1 5-F represents a 40 1~40- 3-pyridyl combination of 710 substituents corresponding to each row of Table B Table 41- 2-Chloro-5- A-1 5-F represents a 41 1~41- pyrimidinyl combination of 710 substituents corresponding to each row of Table B Table 42- 5-Chloropyrazin- A-1 5-F represents a 42 1~42- 2-yl combination of 710 substituents corresponding to each row of Table B Table 43- 6-Chloropyridazin- A-1 5-F represents a 43 1~43- 3-yl combination of 710 substituents corresponding to each row of Table B Table 44- 2-Chloro-5-oxazolyl A-1 5-F represents a 44 1~44- combination of 710 substituents corresponding to each row of Table B Table 45- 6-trifluoromethyl- A-1 5-F represents a 45 1~45- 3-pyridyl combination of 710 substituents corresponding to each row of Table B Table 46- 3-tetrahydrofuranyl A-1 5-F represents a 46 1~46- combination of 710 substituents corresponding to each row of Table B Table 47- 6-Chloro-3-pyridyl A-1 6-F represents a 47 1~47- combination of 710 substituents corresponding to each row of Table B Table 48- 2-Chloro-5-thiazolyl A-1 6-F represents a 48 1~48- combination of 710 substituents corresponding to each row of Table B Table 49- 6-Fluoro-3-pyridyl A-1 6-F represents a 49 1~49- combination of 710 substituents corresponding to each row of Table B Table 50- 6-Bromo-3-pyridyl A-1 6-F represents a 50 1~50- combination of 710 substituents corresponding to each row of Table B Table 51- 6-Chloro-5-fluoro- A-1 6-F represents a 51 1~51- 3-pyridyl combination of 710 substituents corresponding to each row of Table B Table 52- 2-Chloro-5- A-1 6-F represents a 52 1~52- pyrimidinyl combination of 710 substituents corresponding to each row of Table B Table 53- 5-Chloropyrazin- A-1 6-F represents a 53 1~53- 2-yl combination of 710 substituents corresponding to each row of Table B Table 54- 6-Chloropyridazin- A-1 6-F represents a 54 1~54- 3-yl combination of 710 substituents corresponding to each row of Table B Table 55- 2-Chloro-5-oxazolyl A-1 6-F represents a 55 1~55- combination of 710 substituents corresponding to each row of Table B Table 56- 6-trifluoromethyl- A-1 6-F represents a 56 1~56- 3-pyridyl combination of 710 substituents corresponding to each row of Table B Table 57- 3-tetrahydrofuranyl A-1 6-F represents a 57 1~57- combination of 710 substituents corresponding to each row of Table B Table 58- 6-Chloro-3-pyridyl A-1 3-Cl represents a 58 1~58- combination of 710 substituents corresponding to each row of Table B Table 59- 2-Chloro-5-thiazolyl A-1 3-Cl represents a 59 1~59- combination of 710 substituents corresponding to each row of Table B Table 60- 6-Fluoro-3-pyridyl A-1 3-Cl represents a 60 1~60- combination of 710 substituents corresponding to each row of Table B Table 61- 6-Bromo-3-pyridyl A-1 3-Cl represents a 61 1~61- combination of 710 substituents corresponding to each row of Table B Table 62- 6-Chloro-5-fluoro- A-1 3-Cl represents a 62 1~62- 3-pyridyl combination of 710 substituents corresponding to each row of Table B Table 63- 2-Chloro-5- A-1 3-Cl represents a 63 1~63- pyrimidinyl combination of 642 substituents corresponding to each row of Table B Table 64- 5-Chloropyrazin- A-1 3-Cl represents a 64 1~64- 2-yl combination of 710 substituents corresponding to each row of Table B

TABLE 3 Table A Compound No. Ar A Y R Table 65- 6- A-1 3- represents a 65 1~65- Chloropyridazin- Cl combination of 710 3-yl substituents corresponding to each row of Table B Table 66- 2-Chloro-5- A-1 3- represents a 66 1~66- oxazolyl Cl combination of 710 substituents corresponding to each row of Table B Table 67- 6- A-1 3- represents a 67 1~67- trifluoromethyl- Cl combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 68- 3- A-1 3- represents a 68 1~68- tetrahydrofuranyl Cl combination of 710 substituents corresponding to each row of Table B Table 69- 6-Chloro-3- A-1 4- represents a 69 1~69- pyridyl Cl combination of 710 substituents corresponding to each row of Table B Table 70- 2-Chloro-5- A-1 4- represents a 70 1~70- thiazolyl Cl combination of 710 substituents corresponding to each row of Table B Table 71- 6-Fluoro-3- A-1 4- represents a 71 1~71- pyridyl Cl combination of 710 substituents corresponding to each row of Table B Table 72- 6-Bromo-3- A-1 4- represents a 72 1~72- pyridyl Cl combination of 710 substituents corresponding to each row of Table B Table 73- 6-Chloro-5- A-1 4- represents a 73 1~73- fluoro-3- Cl combination of 710 pyridyl substituents corresponding to each row of Table B Table 74- 2-Chloro-5- A-1 4- represents a 74 1~74- pyrimidinyl Cl combination of 710 substituents corresponding to each row of Table B Table 75- 5- A-1 4- represents a 75 1~75- Chloropyrazin- Cl combination of 710 2-yl substituents corresponding to each row of Table B Table 76- 6- A-1 4- represents a 76 1~76- Chloropyridazin- Cl combination of 710 3-yl substituents corresponding to each row of Table B Table 77- 2-Chloro-5- A-1 4- represents a 77 1~77- oxazolyl Cl combination of 710 substituents corresponding to each row of Table B Table 78- 6- A-1 4- represents a 78 1~78- trifluoromethyI- Cl combination of 710 3-pyridyI substituents corresponding to each row of Table B Table 79- 3- A-1 4- represents a 79 1~79- tetrahydrofuranyl Cl combination of 710 substituents corresponding to each row of Table B Table 80- 6-Chloro-3- A-1 5- represents a 80 1~80- pyridyl Cl combination of 710 substituents corresponding to each row of Table B Table 81- 2-Chloro-5- A-1 5- represents a 81 1~81- thiazolyl Cl combination of 710 substituents corresponding to each row of Table B Table 82- 6-Fluoro-3- A-1 5- represents a 82 1~82- pyridyl Cl combination of 710 substituents corresponding to each row of Table B Table 83- 6-Bromo-3- A-1 5- represents a 83 1~83- pyridyl Cl combination of 710 substituents corresponding to each row of Table B Table 84- 6-Chloro-5- A-1 5- represents a 84 1~84- fluoro-3- Cl combination of 710 pyridyl substituents corresponding to each row of Table B Table 85- 2-Chloro-5- A-1 5- represents a 85 1~85- pyrimidinyl Cl combination of 710 substituents corresponding to each row of Table B Table 86- 5- A-1 5- represents a 86 1~86- Chloropyrazin- Cl combination of 710 2-yl substituents corresponding to each row of Table B Table 87- 6- A-1 5- represents a 87 1~87- Chloropyridazin- Cl combination of 710 3-yl substituents corresponding to each row of Table B Table 88- 2-Chloro-5- A-1 5- represents a 88 1~88- oxazolyl Cl combination of 710 substituents corresponding to each row of Table B Table 89-1~89- 6- A-1 5- represents a 89 710 trifluoromethyl- Cl combination of 3-pyridyl substituents corresponding to each row of Table B Table 90- 3- A-1 5- represents a 90 1~90- tetrahydrofuranyl Cl combination of 710 substituents corresponding to each row of Table B Table 91- 6-Chloro-3- A-1 6- represents a 91 1~91- pyridyl Cl combination of 710 substituents corresponding to each row of Table B Table 92- 2-Chloro-5- A-1 6- represents a 92 1~92- thiazolyl Cl combination of 710 substituents corresponding to each row of Table B Table 93- 6-Fluoro-3- A-1 6- represents a 93 1~93- pyridyl Cl combination of 710 substituents corresponding to each row of Table B Table 94- 6-Bromo-3- A-1 6- represents a 94 1~94- pyridyl Cl combination of 710 substituents corresponding to each row of Table B Table 95- 6-Chloro-5- A-1 6- represents a 95 1~95- fluoro-3- Cl combination of 710 pyridyl substituents corresponding to each row of Table B Table 96- 2-Chloro-5- A-1 6- represents a 96 1~96- pyrimidinyl Cl combination of 710 substituents corresponding to each row of Table B

TABLE 4 Table A Compound No. Ar A Y R Table 97- 5- A-1 6- represents a 97 1~97- Chloropyrazin- Cl combination of 710 2-yl substituents corresponding to each row of Table B Table 98- 6- A-1 6- represents a 98 1~98- Chloropyridazin- Cl combination of 710 3-yl substituents corresponding to each row of Table B Table 99- 2-Chloro-5- A-1 6- represents a 99 1~99- oxazolyl Cl combination of 710 substituents corresponding to each row of Table B Table 100- 6- A-1 6- represents a 100 1~100- trifluoromethyI- Cl combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 101- 3- A-1 6- represents a 101 1~101- tetrahydrofuranyl Cl combination of 710 substituents corresponding to each row of Table B Table 102- 6-Chloro-3- A-1 3- represents a 102 1~102- pyridyl CN combination of 710 substituents corresponding to each row of Table B Table 103- 2-Chloro-5- A-1 3- represents a 103 1~103- thiazolyl CN combination of 710 substituents corresponding to each row of Table B Table 104- 6-Fluoro-3- A-1 3- represents a 104 1~104- pyridyl CN combination of 710 substituents corresponding to each row of Table B Table 105- 6-Bromo-3- A-1 3- represents a 105 1~105- pyridyl CN combination of 710 substituents corresponding to each row of Table B Table 106- 6-Chloro-5- A-1 3- represents a 106 1~106- fluoro-3- CN combination of 710 pyridyl substituents corresponding to each row of Table B Table 107- 2-Chloro-5- A-1 3- represents a 107 1~107- pyrimidinyl CN combination of 710 substituents corresponding to each row of Table B Table 108- 5- A-1 3- represents a 108 1~108- Chloropyrazin- CN combination of 710 2-yl substituents corresponding to each row of Table B Table 109- 6- A-1 3- represents a 109 1~109- Chloropyridazin- CN combination of 710 3-yl substituents corresponding to each row of Table B Table 110- 2-Chloro-5- A-1 3- represents a 110 1~110- oxazolyl CN combination of 710 substituents corresponding to each row of Table B Table 111- 6- A-1 3- represents a 111 1~111- trifluoromethyl- CN combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 112- 3- A-1 3- represents a 112 1~112- tetrahydrofuranyl CN combination of 710 substituents corresponding to each row of Table B Table 113- 6-Chloro-3- A-1 4- represents a 113 1~113- pyridyl CN combination of 710 substituents corresponding to each row of Table B Table 114- 2-Chloro-5- A-1 4- represents a 114 1~114- thiazolyl CN combination of 710 substituents corresponding to each row of Table B Table 115- 6-Fluoro-3- A-1 4- represents a 115 1~115- pyridyl CN combination of 710 substituents corresponding to each row of Table B Table 116- 6-Bromo-3- A-1 4- represents a 116 1~116- pyridyl CN combination of 710 substituents corresponding to each row of Table B Table 117- 6-Chloro-5- A-1 4- represents a 117 1~117- Fluoro-3- CN combination of 710 pyridyl substituents corresponding to each row of Table B Table 118- 2-Chloro-5- A-1 4- represents a 118 1~118- pyrimidinyl CN combination of 710 substituents corresponding to each row of Table B Table 119- 5- A-1 4- represents a 119 1~119- Chloropyrazin- CN combination of 710 2-yl substituents corresponding to each row of Table B Table 120- 6- A-1 4- represents a 120 1~120- Chloropyridazin- CN combination of 710 3-yl substituents corresponding to each row of Table B Table 121- 2-Chloro-5- A-1 4- represents a 121 1~121- oxazolyl CN combination of 710 substituents corresponding to each row of Table B Table 122- 6- A-1 4- represents a 122 1~122- trifluoromethyl- CN combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 123- 3- A-1 4- represents a 123 1~123- tetrahydrofuranyl CN combination of 710 substituents corresponding to each row of Table B Table 124- 6-Chloro-3- A-1 5- represents a 124 1~124- pyridyl CN combination of 710 substituents corresponding to each row of Table B Table 125- 2-Chloro-5- A-1 5- represents a 125 1~155- thiazolyl CN combination of 710 substituents corresponding to each row of Table B Table 126- 6-Fluoro-3- A-1 5- represents a 126 1~126- pyridyl CN combination of 710 substituents corresponding to each row of Table B Table 127- 6-Bromo-3- A-1 5- represents a 127 1~127- pyridyl CN combination of 710 substituents corresponding to each row of Table B Table 128- 6-Chloro-5- A-1 5- represents a 128 1~128- fluoro-3- CN combination of 710 pyridyl substituents corresponding to each row of Table B

TABLE 5 Table A Compound No. Ar A Y R Table 129- 2-Chloro-5- A-1 5- represents a 129 1~129- pyrimidinyl CN combination of 710 substituents corresponding to each row of Table B Table 130- 5- A-1 5- represents a 130 1~130- Chloropyrazin- CN combination of 710 2-yl substituents corresponding to each row of Table B Table 131- 6- A-1 5- represents a 131 1~131- Chloropyridazin- CN combination of 710 3-yl substituents corresponding to each row of Table B Table 132- 2-Chloro-5- A-1 5- represents a 132 1~132- oxazolyl CN combination of 710 substituents corresponding to each row of Table B Table 133- 6- A-1 5- represents a 133 1~133- trifluoromethyl- CN combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 134- 3- A-1 5- represents a 134 1~134- tetrahydrofuranyl CN combination of 710 substituents corresponding to each row of Table B Table 135- 6-Chloro-3- A-1 6- represents a 135 1~135- pyridyl CN combination of 710 substituents corresponding to each row of Table B Table 136- 2-Chloro-5- A-1 6- represents a 136 1~136- thiazolyl CN combination of 710 substituents corresponding to each row of Table B Table 137- 6-Fluoro-3- A-1 6- represents a 137 1~137- pyridyl CN combination of 710 substituents corresponding to each row of Table B Table 138- 6-Bromo-3- A-1 6- represents a 138 1~138- pyridyl CN combination of 710 substituents corresponding to each row of Table B Table 139- 6-Chloro-5- A-1 6- represents a 139 1~139- fluoro-3- CN combination of 710 pyridyl substituents corresponding to each row of Table B Table 140-1~140- 2-Chloro-5- A-1 6- represents a 140 710 pyrimidinyl CN combination of substituents corresponding to each row of Table B Table 141- 5- A-1 6- represents a 141 1~141- Chloropyrazin- CN combination of 710 2-yl substituents corresponding to each row of Table B Table 142- 6- A-1 6- represents a 142 1~142- Chloropyridazin- CN combination of 710 3-yl substituents corresponding to each row of Table B Table 143- 2-Chloro-5- A-1 6- represents a 143 1~143- oxazolyl CN combination of 710 substituents corresponding to each row of Table B Table 144- 6- A-1 6- represents a 144 1~144- trifluoromethyl- CN combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 145- 3- A-1 6- represents a 145 1~145- tetrahydrofuranyl CN combination of 710 substituents corresponding to each row of Table B Table 146- 6-Chloro-3- A-1 3- represents a 146 1~146- pyridyl OH combination of 710 substituents corresponding to each row of Table B Table 147- 2-Chloro-5- A-1 3- represents a 147 1~147- thiazolyl OH combination of 710 substituents corresponding to each row of Table B Table 148- 6-Fluoro-3- A-1 3- represents a 148 1~148- pyridyl OH combination of 710 substituents corresponding to each row of Table B Table 149- 6-Bromo-3- A-1 3- represents a 149 1~149- pyridyl OH combination of 710 substituents corresponding to each row of Table B Table 150- 6-Chloro-5- A-1 3- represents a 150 1~150- Fluoro-3- OH combination of 710 pyridyl substituents corresponding to each row of Table B Table 151- 2-Chloro-5- A-1 3- represents a 151 1~151- pyrimidinyl OH combination of 710 substituents corresponding to each row of Table B Table 152- 5- A-1 3- represents a 152 1~152- Chloropyrazin- OH combination of 710 2-yl substituents corresponding to each row of Table B Table 153- 6- A-1 3- represents a 153 1~153- Chloropyridazin- OH combination of 710 3-yl substituents corresponding to each row of Table B Table 154- 2-Chloro-5- A-1 3- represents a 154 1~154- oxazolyl OH combination of 710 substituents corresponding to each row of Table B Table 155- 6- A-1 3- represents a 155 1~155- trifluoromethyl- OH combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 156- 3- A-1 3- represents a 156 1~156- tetrahydrofuranyl OH combination of 710 substituents corresponding to each row of Table B Table 157- 6-Chloro-3- A-1 4- represents a 157 1~157- pyridyl OH combination of 710 substituents corresponding to each row of Table B Table 158- 2-Chloro-5- A-1 4- represents a 158 1~158- thiazolyl OH combination of 710 substituents corresponding to each row of Table B Table 159- 6-Fluoro-3- A-1 4- represents a 159 1~159- pyridyl OH combination of 710 substituents corresponding to each row of Table B Table 160- 6-Bromo-3- A-1 4- represents a 160 1~160- pyridyl OH combination of 710 substituents corresponding to each row of Table B

TABLE 6 Table A Compound No. Ar A Y R Table 161- 6-Chloro-5- A-1 4- represents a 161 1~161- fluoro-3- OH combination of 710 pyridyl substituents corresponding to each row of Table B Table 162- 2-Chloro-5- A-1 4- represents a 162 1~162- pyrimidinyl OH combination of 710 substituents corresponding to each row of Table B Table 163- 5- A-1 4- represents a 163 1~163- Chloropyrazin- OH combination of 710 2-yl substituents corresponding to each row of Table B Table 164- 6- A-1 4- represents a 164 1~164- Chloropyridazin- OH combination of 710 3-yl substituents corresponding to each row of Table B Table 165- 2-Chloro-5- A-1 4- represents a 165 1~165- oxazolyl OH combination of 710 substituents corresponding to each row of Table B Table 166- 6- A-1 4- represents a 166 1~166- trifluoromethyl- OH combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 167- 3- A-1 4- represents a 167 1~167- tetrahydrofuranyl OH combination of 710 substituents corresponding to each row of Table B Table 168- 6-Chloro-3- A-1 5- represents a 168 1~168- pyridyl OH combination of 710 substituents corresponding to each row of Table B Table 169- 2-Chloro-5- A-1 5- represents a 169 1~169- thiazolyl OH combination of 710 substituents corresponding to each row of Table B Table 170- 6-Fluoro-3- A-1 5- represents a 170 1~170- pyridyl OH combination of 710 substituents corresponding to each row of Table B Table 171- 6-Bromo-3- A-1 5- represents a 171 1~171- pyridyl OH combination of 710 substituents corresponding to each row of Table B Table 172- 6-Chloro-5- A-1 5- represents a 172 1~172- fluoro-3- OH combination of 710 pyridyl substituents corresponding to each row of Table B Table 173- 2-Chloro-5- A-1 5- represents a 173 1~173- pyrimidinyl OH combination of 710 substituents corresponding to each row of Table B Table 174- 5- A-1 5- represents a 174 1~174- Chloropyrazin- OH combination of 710 2-yl substituents corresponding to each row of Table B Table 175- 6- A-1 5- represents a 175 1~175- Chloropyridazin- OH combination of 710 3-yl substituents corresponding to each row of Table B Table 176- 2-Chloro-5- A-1 5- represents a 176 1~176- oxazolyl OH combination of 710 substituents corresponding to each row of Table B Table 177- 6- A-1 5- represents a 177 1~177- trifluoromethyl- OH combination of 710 3-pyridyI substituents corresponding to each row of Table B Table 178- 3- A-1 5- represents a 178 1~178- tetrahydrofuranyl OH combination of 710 substituents corresponding to each row of Table B Table 179- 6-Chloro-3- A-1 6- represents a 179 1~179- pyridyl OH combination of 710 substituents corresponding to each row of Table B Table 180- 2-Chloro-5- A-1 6- represents a 180 1~180- thiazolyl OH combination of 710 substituents corresponding to each row of Table B Table 181- 6-Fluoro-3- A-1 6- represents a 181 1~181- pyridyl OH combination of 710 substituents corresponding to each row of Table B Table 182- 6-Bromo-3- A-1 6- represents a 182 1~182- pyridyl OH combination of 710 substituents corresponding to each row of Table B Table 183- 6-Chloro-5- A-1 6- represents a 183 1~183- fluoro-3- OH combination of 710 pyridyl substituents corresponding to each row of Table B Table 184- 2-Chloro-5- A-1 6- represents a 184 1~184- pyrimidinyl OH combination of 710 substituents corresponding to each row of Table B Table 185- 5- A-1 6- represents a 185 1~185- Chloropyrazin- OH combination of 710 2-yl substituents corresponding to each row of Table B Table 186- 6- A-1 6- represents a 186 1~186- Chloropyridazin- OH combination of 710 3-yl substituents corresponding to each row of Table B Table 187- 2-Chloro-5- A-1 6- represents a 187 1~187- oxazolyl OH combination of 710 substituents corresponding to each row of Table B Table 188- 6- A-1 6- represents a 188 1~188- trifluoromethyl- OH combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 189- 3- A-1 6- represents a 189 1~189- tetrahydrofuranyl OH combination of 710 substituents corresponding to each row of Table B Table 190- 6-Chloro-3- A- H represents a 190 1~190- pyridyl 13 combination of 710 substituents corresponding to each row of Table B Table 191- 2-Chloro-5- A- H represents a 191 1~191- thiazolyl 13 combination of 710 substituents corresponding to each row of Table B Table 192- 6-Fluoro-3- A- H represents a 192 1~192- pyridyl 13 combination of 710 substituents corresponding to each row of Table B

TABLE 7 Table A Compound No. Ar A Y R Table 193- 6-Bromo-3- A-13 H represents a 193 1~193- pyridyl combination of 710 substituents corresponding to each row of Table B Table 194- 6-Chloro-5- A-13 H represents a 194 1~194- fluoro-3- combination of 710 pyridyl substituents corresponding to each row of Table B Table 195- 2-Chloro-5- A-13 H represents a 195 1~195- pyrimidinyl combination of 710 substituents corresponding to each row of Table B Table 196- 5-Chloropyrazin- A-13 H represents a 196 1~196- 2-yl combination of 710 substituents corresponding to each row of Table B Table 197- 6-Chloropyridazin- A-13 H represents a 197 1~197- 3-yl combination of 710 substituents corresponding to each row of Table B Table 198- 2-Chloro-5- A-13 H represents a 198 1~198- oxazolyl combination of 710 substituents corresponding to each row of Table B Table 199- 6-trifluoromethyl- A-13 H represents a 199 1~199- 3-pyridyl combination of 710 substituents corresponding to each row of Table B Table 200- 3- A-13 H represents a 200 1~200- tetrahydrofuranyl combination of 710 substituents corresponding to each row of Table B Table 201- 6-Chloro-3- A-14 H represents a 201 1~201- pyridyl combination of 710 substituents corresponding to each row of Table B Table 202- 2-Chloro-5- A-14 H represents a 202 1~202- thiazolyl combination of 710 substituents corresponding to each row of Table B Table 203- 6-Fluoro-3- A-14 H represents a 203 1~203- pyridyl combination of 710 substituents corresponding to each row of Table B Table 204- 6-Bromo-3- A-14 H represents a 204 1~204- pyridyl combination of 710 substituents corresponding to each row of Table B Table 205- 6-Chloro-5- A-14 H represents a 205 1~205- fluoro-3- combination of 710 pyridyl substituents corresponding to each row of Table B Table 206- 2-Chloro-5- A-14 H represents a 206 1~206- pyrimidinyl combination of 710 substituents corresponding to each row of Table B Table 207- 5-Chloropyrazin- A-14 H represents a 207 1~207- 2-yl combination of 710 substituents corresponding to each row of Table B Table 208- 6-Chloropyridazin- A-14 H represents a 208 1~208- 3-yl combination of 710 substituents corresponding to each row of Table B Table 209- 2-Chloro-5- A-14 H represents a 209 1~209- oxazolyl combination of 710 substituents corresponding to each row of Table B Table 210- 6-trifluoromethyl- A-14 H represents a 210 1~210- 3-pyridyl combination of 710 substituents corresponding to each row of Table B Table 211- 3-tetrahydrofuranyl A-14 H represents a 211 1~211- combination of 710 substituents corresponding to each row of Table B Table 212- 6-Chloro-3- A-15 H represents a 212 1~212- pyridyl combination of 710 substituents corresponding to each row of Table B Table 213- 2-Chloro-5- A-15 H represents a 213 1~213- thiazolyl combination of 710 substituents corresponding to each row of Table B Table 214- 6-Fluoro-3- A-15 H represents a 214 1~214- pyridyl combination of 710 substituents corresponding to each row of Table B Table 215- 6-Bromo-3- A-15 H represents a 215 1~215- pyridyl combination of 710 substituents corresponding to each row of Table B Table 216- 6-Chloro-5- A-15 H represents a 216 1~216- fluoro-3- combination of 710 pyridyl substituents corresponding to each row of Table B Table 217- 2-Chloro-5- A-15 H represents a 217 1~217- pyrimidinyl combination of 710 substituents corresponding to each row of Table B Table 218- 5- A-15 H represents a 218 1~218- Chloropyrazin combination of 710 -2-yl substituents corresponding to each row of Table B Table 219- 6- A-15 H represents a 219 1~219- Chloropyridazin- combination of 710 3-yl substituents corresponding to each row of Table B Table 220- 2-Chloro-5- A-15 H represents a 220 1~220- oxazolyl combination of 710 substituents corresponding to each row of Table B Table 221- 6- A-15 H represents a 221 1~221- trifluoromethyl- combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 222- 3- A-15 H represents a 222 1~222- tetrahydrofuranyl combination of 710 substituents corresponding to each row of Table B Table 223- 6-Chloro-3- A-16 H represents a 223 1~223- pyridyl combination of 710 substituents corresponding to each row of Table B Table 224- 2 -Chloro-5- A-16 H represents a 224 1~224- thiazolyl combination of 710 substituents corresponding to each row of Table B

TABLE 8 Table A Compound No. Ar A Y R Table 225- 6-Fluoro-3- A-16 H represents a 225 1~225- pyridyl combination of 710 substituents corresponding to each row of Table B Table 226- 6-Bromo-3- A-16 H represents a 226 1~226- pyridyl combination of 710 substituents corresponding to each row of Table B Table 227- 6-Chloro-5- A-16 H represents a 227 1~227- fluoro-3- combination of 710 pyridyl substituents corresponding to each row of Table B Table 228- 2-Chloro-5- A-16 H represents a 228 1~228- pyrimidinyl combination of 710 substituents corresponding to each row of Table B Table 229- 5- A-16 H represents a 229 1~229- Chloropyrazin- combination of 710 2-yl substituents corresponding to each row of Table B Table 230- 6- A-16 H represents a 230 1~230- Chloropyridazin- combination of 710 3-yl substituents corresponding to each row of Table B Table 231- 2-Chloro-5- A-16 H represents a 231 1~231- oxazolyl combination of 710 substituents corresponding to each row of Table B Table 232- 6- A-16 H represents a 232 1~232- trifluoromethyl- combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 233- 3- A-16 H represents a 233 1~233- tetrahydrofuranyl combination of 710 substituents corresponding to each row of Table B Table 234- 6-Chloro-3- A-2 H represents a 234 1~234- pyridyl combination of 710 substituents corresponding to each row of Table B Table 235- 6-Chloro-3- A-3 H represents a 235 1~235- pyridyl combination of 710 substituents corresponding to each row of Table B Table 236- 6-Chloro-3- A-4 H represents a 236 1~236- pyridyl combination of 710 substituents corresponding to each row of Table B Table 237- 6-Chloro-3- A-5 H represents a 237 1~237- pyridyl combination of 710 substituents corresponding to each row of Table B Table 238- 6-Chloro-3- A-6 H represents a 238 1~238- pyridyl combination of 710 substituents corresponding to each row of Table B Table 239- 6-Chloro-3- A-7 H represents a 239 1~239- pyridyl combination of 710 substituents corresponding to each row of Table B Table 240- 6-Chloro-3- A-8 H represents a 240 1~240- pyridyl combination of 710 substituents corresponding to each row of Table B Table 241- 6-Chloro-3- A-9 H represents a 241 1~241- pyridyl combination of 710 substituents corresponding to each row of Table B Table 242- 6-Chloro-3- A-10 H represents a 242 1~242- pyridyl combination of 710 substituents corresponding to each row of Table B Table 243- 6-Chloro-3- A-11 H represents a 243 1~243- pyridyl combination of 710 substituents corresponding to each row of Table B Table 244- 6-Chloro-3- A-12 H represents a 244 1~244- pyridyl combination of 710 substituents corresponding to each row of Table B Table 245- 6-Chloro-3- A-17 H represents a 245 1~245- pyridyl combination of 710 substituents corresponding to each row of Table B Table 246- 6-Chloro-3- A-18 H represents a 246 1~246- pyridyl combination of 710 substituents corresponding to each row of Table B Table 247- 6-Chloro-3- A-19 H represents a 247 1~247- pyridyl combination of 710 substituents corresponding to each row of Table B Table 248- 6-Chloro-3- A-20 H represents a 248 1~248- pyridyl combination of 710 substituents corresponding to each row of Table B Table 249- 6-Chloro-3- A-21 H represents a 249 1~249- pyridyl combination of 710 substituents corresponding to each row of Table B Table 250- 6-Chloro-3- A-22 H represents a 250 1~250- pyridyl combination of 710 substituents corresponding to each row of Table B Table 251- 6-Chloro-3- A-23 H represents a 251 1~251- pyridyl combination of 710 substituents corresponding to each row of Table B Table 252- 6-Chloro-3- A-24 H represents a 252 1~252- pyridyl combination of 710 substituents corresponding to each row of Table B Table 253- 6-Chloro-3- A-25 H represents a 253 1~253- pyridyl combination of 710 substituents corresponding to each row of Table B Table 254- 6-Chloro-3- A-26 H represents a 254 1~254- pyridyl combination of 710 substituents corresponding to each row of Table B Table 255- 6-Chloro-3- A-27 H represents a 255 1~255- pyridyl combination of 710 substituents corresponding to each row of Table B Table 256- 6-Chloro-3- A-28 H represents a 256 1~256- pyridyl combination of 710 substituents corresponding to each row of Table B

TABLE 9 Table A Compound No. Ar A Y R Table 257- 6-Chloro-3- A-29 H represents a 257 1~257- pyridyl combination of 710 substituents corresponding to each row of Table B Table 258- 6-Chloro-3- A-30 H represents a 258 1~258- pyridyl combination of 710 substituents corresponding to each row of Table B Table 259- 6-Chloro-3- A-31 H represents a 259 1~259- pyridyl combination of 710 substituents corresponding to each row of Table B Table 260- 6-Chloro-3- A-32 H represents a 260 1~260- pyridyl combination of 710 substituents corresponding to each row of Table B Table 261- 6-Chloro-3- A-33 H represents a 261 1~261- pyridyl combination of 710 substituents corresponding to each row of Table B Table 262- 6-Chloro-3- A-34 H represents a 262 1~262- pyridyl combination of 710 substituents corresponding to each row of Table B Table 263- 6-Chloro-3- A-35 H represents a 263 1~263- pyridyl combination of 710 substituents corresponding to each row of Table B Table 264- 6-Chloro-3- A-36 H represents a 264 1~264- pyridyl combination of 710 substituents corresponding to each row of Table B Table 265- 6-Chloro-3- A-37 H represents a 265 1~265- pyridyl combination of 710 substituents corresponding to each row of Table B Table 266- 6-Chloro-3- A-38 H represents a 266 1~266- pyridyl combination of 710 substituents corresponding to each row of Table B Table 267- 6-Chloro-3- A-39 H represents a 267 1~267- pyridyl combination of 710 substituents corresponding to each row of Table B Table 268- 6-Chloro-3- A-40 H represents a 268 1~268- pyridyl combination of 710 substituents corresponding to each row of Table B Table 269- 6-Chloro-3- A-2 H represents a 269 1~269- pyridyl combination of 710 substituents corresponding to each row of Table B Table 270- 6-Chloro-3- A-3 H represents a 270 1~270- pyridyl combination of 710 substituents corresponding to each row of Table B Table 271- 6-Chloro-3- A-4 H represents a 271 1~271- pyridyl combination of 710 substituents corresponding to each row of Table B Table 272- 6-Chloro-3- A-5 H represents a 272 1~272- pyridyl combination of 710 substituents corresponding to each row of Table B Table 273- 6-Chloro-3- A-6 H represents a 273 1~273- pyridyl combination of 710 substituents corresponding to each row of Table B Table 274- 6-Chloro-3- A-7 H represents a 274 1~274- pyridyl combination of 710 substituents corresponding to each row of Table B Table 275- 6-Chloro-3- A-8 H represents a 275 1~275- pyridyl combination of 710 substituents corresponding to each row of Table B Table 276- 6-Chloro-3- A-9 H represents a 276 1~276- pyridyl combination of 710 substituents corresponding to each row of Table B Table 277- 6-Chloro-3- A-10 H represents a 277 1~277- pyridyl combination of 710 substituents corresponding to each row of Table B Table 278- 6-Chloro-3- A-11 H represents a 278 1~278- pyridyl combination of 710 substituents corresponding to each row of Table B Table 279- 6-Chloro-3- A-12 H represents a 279 1~279- pyridyl combination of 710 substituents corresponding to each row of Table B Table 280- 6-Chloro-3- A-17 H represents a 280 1~280- pyridyl combination of 710 substituents corresponding to each row of Table B Table 281- 6-Chloro-3- A-18 H represents a 281 1~281- pyridyl combination of 710 substituents corresponding to each row of Table B Table 282- 6-Chloro-3- A-19 H represents a 282 1~282- pyridyl combination of 710 substituents corresponding to each row of Table B Table 283- 6-Chloro-3- A-20 H represents a 283 1~283- pyridyl combination of 710 substituents corresponding to each row of Table B Table 284- 6-Chloro-3- A-21 H represents a 284 1~284- pyridyl combination of 710 substituents corresponding to each row of Table B Table 285- 6-Chloro-3- A-22 H represents a 285 1~285- pyridyl combination of 710 substituents corresponding to each row of Table B Table 286- 6-Chloro-3- A-23 H represents a 286 1~286- pyridyl combination of 710 substituents corresponding to each row of Table B Table 287- 6-Chloro-3- A-24 H represents a 287 1~287- pyridyl combination of 710 substituents corresponding to each row of Table B Table 288- 6-Chloro-3- A-25 H represents a 288 1~288- pyridyl combination of 710 substituents corresponding to each row of Table B

TABLE 10 Table A Compound No. Ar A Y R Table 289- 6-Chloro-3- A-26 H represents a 289 1~289- pyridyl combination of 710 substituents corresponding to each row of Table B Table 290- 6-Chloro-3- A-27 H represents a 290 1~290- pyridyl combination of 710 substituents corresponding to each row of Table B Table 291- 6-Chloro-3- A-28 H represents a 291 1~291- pyridyl combination of 710 substituents corresponding to each row of Table B Table 292- 6-Chloro-3- A-29 H represents a 292 1~292- pyridyl combination of 710 substituents corresponding to each row of Table B Table 293- 6-Chloro-3- A-30 H represents a 293 1~293- pyridyl combination of 710 substituents corresponding to each row of Table B Table 294- 6-Chloro-3- A-31 H represents a 294 1~294- pyridyl combination of 710 substituents corresponding to each row of Table B Table 295- 6-Chloro-3- A-32 H represents a 295 1~295- pyridyl combination of 710 substituents corresponding to each row of Table B Table 296- 6-Chloro-3- A-33 H represents a 296 1~296- pyridyl combination of 710 substituents corresponding to each row of Table B Table 297- 6-Chloro-3- A-34 H represents a 297 1~297- pyridyl combination of 710 substituents corresponding to each row of Table B Table 298- 6-Chloro-3- A-35 H represents a 298 1~298- pyridyl combination of 710 substituents corresponding to each row of Table B Table 299- 6-Chloro-3- A-36 H represents a 299 1~299- pyridyl combination of 710 substituents corresponding to each row of Table B Table 300- 6-Chloro-3- A-37 H represents a 300 1~300- pyridyl combination of 710 substituents corresponding to each row of Table B Table 301- 6-Chloro-3- A-38 H represents a 301 1~301- pyridyl combination of 710 substituents corresponding to each row of Table B Table 302- 6-Chloro-3- A-39 H represents a 302 1~302- pyridyl combination of 710 substituents corresponding to each row of Table B Table 303- 6-Chloro-3- A-40 H represents a 303 1~303- pyridyl combination of 710 substituents corresponding to each row of Table B Table 304- 6-Chloro-3- A-2 H represents a 304 1~304- pyridyl combination of 710 substituents corresponding to each row of Table B Table 305- 6-Chloro-3- A-3 H represents a 305 1~305- pyridyl combination of 710 substituents corresponding to each row of Table B Table 306- 6-Chloro-3- A-4 H represents a 306 1~306- pyridyl combination of 710 substituents corresponding to each row of Table B Table 307- 6-Chloro-3- A-5 H represents a 307 1~307- pyridyl combination of 710 substituents corresponding to each row of Table B Table 308- 6-Chloro-3- A-6 H represents a 308 1~308- pyridyl combination of 710 substituents corresponding to each row of Table B Table 309- 6-Chloro-3- A-7 H represents a 309 1~309- pyridyl combination of 710 substituents corresponding to each row of Table B Table 310- 6-Chloro-3- A-8 H represents a 310 1~310- pyridyl combination of 710 substituents corresponding to each row of Table B Table 311- 6-Chloro-3- A-9 H represents a 311 1~311- pyridyl combination of 710 substituents corresponding to each row of Table B Table 312- 6-Chloro-3- A-10 H represents a 312 1~312- pyridyl combination of 710 substituents corresponding to each row of Table B Table 313- 6-Chloro-3- A-11 H represents a 313 1~313- pyridyl combination of 710 substituents corresponding to each row of Table B Table 314- 6-Chloro-3- A-12 H represents a 314 1~314- pyridyl combination of 710 substituents corresponding to each row of Table B Table 315- 6-Chloro-3- A-17 H represents a 315 1~315- pyridyl combination of 710 substituents corresponding to each row of Table B Table 316- 6-Chloro-3- A-18 H represents a 316 1~316- pyridyl combination of 710 substituents corresponding to each row of Table B Table 317- 6-Chloro-3- A-19 H represents a 317 1~317- pyridyl combination of 710 substituents corresponding to each row of Table B Table 318- 6-Chloro-3- A-20 H represents a 318 1~318- pyridyl combination of 710 substituents corresponding to each row of Table B Table 319- 6-Chloro-3- A-21 H represents a 319 1~319- pyridyl combination of 710 substituents corresponding to each row of Table B Table 320- 6-Chloro-3- A-22 H represents a 320 1~320- pyridyl combination of 710 substituents corresponding to each row of Table B

TABLE 11 Table A Compound No Ar A Y R Table 321- 6-Chloro-3- A-23 H represents a 321 1~321- pyridyl combination of 710 substituents corresponding to each row of Table B Table 322- 6-Chloro-3- A-24 H represents a 322 1~322- pyridyl combination of 710 substituents corresponding to each row of Table B Table 323- 6-Chloro-3- A-25 H represents a 323 1~323- pyridyl combination of 710 substituents corresponding to each row of Table B Table 324- 6-Chloro-3- A-26 H represents a 324 1~324- pyridyl combination of 710 substituents corresponding to each row of Table B Table 325- 6-Chloro-3- A-27 H represents a 325 1~325- pyridyl combination of 710 substituents corresponding to each row of Table B Table 326- 6-Chloro-3- A-28 H represents a 326 1~326- pyridyl combination of 710 substituents corresponding to each row of Table B Table 327- 6-Chloro-3- A-29 H represents a 327 1~327- pyridyl combination of 710 substituents corresponding to each row of Table B Table 328- 6-Chloro-3- A-30 H represents a 328 1~328- pyridyl combination of 710 substituents corresponding to each row of Table B Table 329- 6-Chloro-3- A-31 H represents a 329 1~329- pyridyl combination of 710 substituents corresponding to each row of Table B Table 330- 6-Chloro-3- A-32 H represents a 330 1~330- pyridyl combination of 710 substituents corresponding to each row of Table B Table 331- 6-Chloro-3- A-33 H represents a 331 1~331- pyridyl combination of 710 substituents corresponding to each row of Table B Table 332- 6-Chloro-3- A-34 H represents a 332 1~332- pyridyl combination of 710 substituents corresponding to each row of Table B Table 333- 6-Chloro-3- A-35 H represents a 333 1~333- pyridyl combination of 710 substituents corresponding to each row of Table B Table 334- 6-Chloro-3- A-36 H represents a 334 1~334- pyridyl combination of 710 substituents corresponding to each row of Table B Table 335- 6-Chloro-3- A-37 H represents a 335 1~335- pyridyl combination of 710 substituents corresponding to each row of Table B Table 336- 6-Chloro-3- A- H represents a 336 1~336- pyridyl 38 combination of 710 substituents corresponding to each row of Table B Table 337- 6-Chloro-3- A-39 H represents a 337 1~337- pyridyl combination of 710 substituents corresponding to each row of Table B Table 338- 6-Chloro-3- A-40 H represents a 338 1~338- pyridyl combination of 710 substituents corresponding to each row of Table B Table 339- 2-Chloro-5- A-2 H represents a 339 1~339- thiazolyl combination of 710 substituents corresponding to each row of Table B Table 340- 3- A-3 H represents a 340 1~340- Trifluorometh combination of 710 ylphenyl substituents corresponding to each row of Table B Table 341- 2- A-4 H represents a 341 1~341- Methylphenyl combination of 710 substituents corresponding to each row of Table B Table 342- 3- A-5 H represents a 342 1~342- Methylphenyl combination of 710 substituents corresponding to each row of Table B Table 343- 4- A-6 H represents a 343 1~343- Methylphenyl combination of 710 substituents corresponding to each row of Table B Table 344- 4- A-7 H represents a 344 1~344- Trifluorometh combination of 710 ylphenyl substituents corresponding to each row of Table B Table 345- 2- A-8 H represents a 345 1~345- Trifluorometh combination of 710 ylphenyl substituents corresponding to each row of Table B Table 346- 2- A-9 H represents a 346 1~346- Methoxyphenyl combination of 710 substituents corresponding to each row of Table B Table 347- 3- A-10 H represents a 347 1~347- Methoxyphenyl combination of 710 substituents corresponding to each row of Table B Table 348- 4- A-11 H represents a 348 1~348- Methoxyphenyl combination of 710 substituents corresponding to each row of Table B Table 349- 2-Cyanophenyl A-12 H represents a 349 1~349- combination of 710 substituents corresponding to each row of Table B Table 350- 3-Cyanophenyl A-17 H represents a 350 1~350- combination of 710 substituents corresponding to each row of Table B Table 351- 4-Cyanophenyl A-18 H represents a 351 1~351- combination of 710 substituents corresponding to each row of Table B Table 352- 2-Nitrophenyl A-19 H represents a 352 1~352- combination of 710 substituents corresponding to each row of Table B

TABLE 12 Table A Compound No Ar A Y R Table 353- 3-Nitrophenyl A-20 H represents a 353 1~353- combination of 710 substituents corresponding to each row of Table B Table 354- 4-Nitrophenyl A-21 H represents a 354 1~354- combination of 710 substituents corresponding to each row of Table B Table 355- 3-Hydroxy-2- A-22 H represents a 355 1~355- pyridyl combination of 710 substituents corresponding to each row of Table B Table 356- 4-hydroxy-2- A-23 H represents a 356 1~356- pyridyl combination of 710 substituents corresponding to each row of Table B Table 357- 5-hydroxy-2- A-24 H represents a 357 1~357- pyridyl combination of 710 substituents corresponding to each row of Table B Table 358- 6-hydroxy-2- A-25 H represents a 358 1~358- pyridyl combination of 710 substituents corresponding to each row of Table B Table 359- 2-Hydroxy-3- A-26 H represents a 359 1~359- pyridyl combination of 710 substituents corresponding to each row of Table B Table 360- 5-Hydroxy-3- A-27 H represents a 360 1~360- pyridyl combination of 710 substituents corresponding to each row of Table B Table 361- 6-Hydroxy-3- A-28 H represents a 361 1~361- pyridyl combination of 710 substituents corresponding to each row of Table B Table 362- 4-Hydroxy-3- A-29 H represents a 362 1~362- pyridyl combination of 710 substituents corresponding to each row of Table B Table 363- 2-Hydroxy-4- A-30 H represents a 363 1~363- pyridyl combination of 710 substituents corresponding to each row of Table B Table 364- 3-Hydroxy-4- A-31 H represents a 364 1~364- pyridyl combination of 710 substituents corresponding to each row of Table B Table 365- 3-Chloro-2- A-32 H represents a 365 1~365- pyridyl combination of 710 substituents corresponding to each row of Table B Table 366- 4-Chloro-2- A-33 H represents a 366 1~366- pyridyl combination of 710 substituents corresponding to each row of Table B Table 367- 5-Chloro-2- A-34 H represents a 367 1~367- pyridyl combination of 710 substituents corresponding to each row of Table B Table 368- 6-Chloro-2- A-35 H represents a 368 1~368- pyridyl combination of 710 substituents corresponding to each row of Table B Table 369- 2-Chloro-3- A-36 H represents a 369 1~369- pyridyl combination of 710 substituents corresponding to each row of Table B Table 370- 5-Chloro-3- A-37 H represents a 370 1~370- pyridyl combination of 710 substituents corresponding to each row of Table B Table 371- 6-Chloro-3- A-38 H represents a 371 1~371- pyridyl combination of 710 substituents corresponding to each row of Table B Table 372- 4-Chloro-3- A-39 H represents a 372 1~372- pyridyl combination of 710 substituents corresponding to each row of Table B Table 373- 2-Chloro-4- A-40 H represents a 373 1~373- pyridyl combination of 710 substituents corresponding to each row of Table B Table 374- 3-Chloro-4- A-2 H represents a 374 1~374- pyridyl combination of 710 substituents corresponding to each row of Table B Table 375- 3-bromo-2- A-3 H represents a 375 1~375- pyridyl combination of 710 substituents corresponding to each row of Table B Table 376- 4-bromo-2- A-4 H represents a 376 1~376- pyridyl combination of 710 substituents corresponding to each row of Table B Table 377- 5-bromo-2- A-5 H represents a 377 1~377- pyridyl combination of 710 substituents corresponding to each row of Table B Table 378- 6-bromo-2- A-6 H represents a 378 1~378- pyridyl combination of 710 substituents corresponding to each row of Table B Table 379- 2-bromo-3- A-7 H represents a 379 1~379- pyridyl combination of 710 substituents corresponding to each row of Table B Table 380- 5-bromo-3- A-8 H represents a 380 1~380- pyridyl combination of 710 substituents corresponding to each row of Table B Table 381- 6-bromo-3- A-9 H represents a 381 1~381- pyridyl combination of 710 substituents corresponding to each row of Table B Table 382- 4-bromo-3- A-10 H represents a 382 1~382- pyridyl combination of 710 substituents corresponding to each row of Table B Table 383- 2-bromo-4- A-11 H represents a 383 1~383- pyridyl combination of 710 substituents corresponding to each row of Table B Table 384- 3-bromo-4- A-12 H represents a 384 1~384- pyridyl combination of 710 substituents corresponding to each row of Table B

TABLE 13 Table A Compound No Ar A Y R Table 385- 3-Fluoro-2- A-17 H represents a 385 1~385- pyridyl combination of 710 substituents corresponding to each row of Table B Table 386- 4-Fluoro-2- A-18 H represents a 386 1~386- pyridyl combination of 710 substituents corresponding to each row of Table B Table 387- 5-Fluoro-2- A-19 H represents a 387 1~387- pyridyl combination of 710 substituents corresponding to each row of Table B Table 388- 6-Fluoro-2- A-20 H represents a 388 1~388- pyridyl combination of 710 substituents corresponding to each row of Table B Table 389- 2-Fluoro-3- A-21 H represents a 389 1~389- pyridyl combination of 710 substituents corresponding to each row of Table B Table 390- 5-Fluoro-3- A-22 H represents a 390 1~390- pyridyl combination of 710 substituents corresponding to each row of Table B Table 391- 6-Fluoro-3- A-23 H represents a 391 1~391- pyridyl combination of 710 substituents corresponding to each row of Table B Table 392- 4-Fluoro-3- A-24 H represents a 392 1~392- pyridyl combination of 710 substituents corresponding to each row of Table B Table 393- 2-Fluoro-4- A-25 H represents a 393 1~393- pyridyl combination of 710 substituents corresponding to each row of Table B Table 394- 3-Fluoro-4- A-26 H represents a 394 1~394- pyridyl combination of 710 substituents corresponding to each row of Table B Table 395- 6-Fluoro-3- A-27 H represents a 395 1~395- pyridyl combination of 710 substituents corresponding to each row of Table B Table 396- 3-iodo-2- A-28 H represents a 396 1~396- pyridyl combination of 710 substituents corresponding to each row of Table B Table 397- 4-iodo-2- A-29 H represents a 397 1~397- pyridyl combination of 710 substituents corresponding to each row of Table B Table 398- 5-iodo-2- A-30 H represents a 398 1~398- pyridyl combination of 710 substituents corresponding to each row of Table B Table 399- 6-iodo- A-31 H represents a 399 1~399- 2~pyridyl combination of 710 substituents corresponding to each row of Table B Table 400- 2-iodo-3- A-32 H represents a 400 1~400- pyridyl combination of 710 substituents corresponding to each row of Table B Table 401- 5-iodo-3- A-33 H represents a 401 1~401- pyridyl combination of 710 substituents corresponding to each row of Table B Table 402- 6-iodo-3- A-34 H represents a 402 1~402- pyridyl combination of 710 substituents corresponding to each row of Table B Table 403- 4-iodo-3- A-35 H represents a 403 1~403- pyridyl combination of 710 substituents corresponding to each row of Table B Table 404- 2-iodo-4- A-36 H represents a 404 1~404- pyridyl combination of 710 substituents corresponding to each row of Table B Table 405- 3-iodo-4- A-37 H represents a 405 1~405- pyridyl combination of 710 substituents corresponding to each row of Table B Table 406- 6-iodo-3- A-38 H represents a 406 1~406- pyridyl combination of 710 substituents corresponding to each row of Table B Table 407- 6-iodo-3- A-39 H represents a 407 1~407- pyridyl combination of 710 substituents corresponding to each row of Table B Table 408- 2- A-40 H represents a 408 1~408- tetrahydrofuranyl combination of 710 substituents corresponding to each row of Table B Table 409- 3- A-2 H represents a 409 1~409- tetrahydrofuranyl combination of 710 substituents corresponding to each row of Table B Table 410- 5-Chloro-2- A-3 H represents a 410 1~410- thiazolyl combination of 710 substituents corresponding to each row of Table B Table 411- 6-Fluoro-3- A-4 H represents a 411 1~411- pyridyl combination of 710 substituents corresponding to each row of Table B Table 412- 6-Bromo-3- A-5 H represents a 412 1~412- pyridyl combination of 710 substituents corresponding to each row of Table B Table 413- 6-Chloro-5- A-6 H represents a 413 1~413- Fluoro-3- combination of 710 pyridyl substituents corresponding to each row of Table B Table 414- 3,5- A-7 H represents a 414 1~414- Dimethylphenyl combination of 710 substituents corresponding to each row of Table B Table 415- 2,3- A-8 H represents a 415 1~415- Dimethylphenyl combination of 710 substituents corresponding to each row of Table B Table 416- 2,4- A-9 H represents a 416 1~416- Dimethyophenyl combination of 710 substituents corresponding to each row of Table B

TABLE 14 Table A Compound No Ar A Y R Table 417- Phenyl A-10 H represents a 417 1~417- combination of 710 substituents corresponding to each row of Table B Table 418- cyclopentyl A-11 H represents a 418 1~418- combination of 710 substituents corresponding to each row of Table B Table 419- cyclohexyl A-12 H represents a 419 1~419- combination of 710 substituents corresponding to each row of Table B Table 420- 3- A-17 H represents a 420 1~420- methylcyclohexyl combination of 710 substituents corresponding to each row of Table B Table 421- cyclobutyl A-18 H represents a 421 1~421- combination of 710 substituents corresponding to each row of Table B Table 422- 2-oxetanyl A-19 H represents a 422 1~422- combination of 710 substituents corresponding to each row of Table B Table 423- 3-oxetanyl A-20 H represents a 423 1~423- combination of 710 substituents corresponding to each row of Table B Table 424- 2-thietanyl A-21 H represents a 424 1~424- combination of 710 substituents corresponding to each row of Table B Table 425- 3-thietanyl A-22 H represents a 425 1~425- combination of 710 substituents corresponding to each row of Table B Table 426- 2-azetidinyl A-23 H represents a 426 1~426- combination of 710 substituents corresponding to each row of Table B Table 427- 3-azetidinyl A-24 H represents a 427 1~427- combination of 710 substituents corresponding to each row of Table B Table 428- 6-iodo-3- A-25 H represents a 428 1~428- pyridyl combination of 710 substituents corresponding to each row of Table B Table 429- 6-iodo-3- A-26 H represents a 429 1~429- pyridyl combination of 710 substituents corresponding to each row of Table B Table 430- 2- A-27 H represents a 430 1~430- tetrahydrofuranyl combination of 710 substituents corresponding to each row of Table B Table 431- 2-Chloro-3- A-28 H represents a 431 1~431- pyridyl combination of 710 substituents corresponding to each row of Table B Table 432- 5-Chloro-3- A-29 H represents a 432 1~432- pyridyl combination of 710 substituents corresponding to each row of Table B Table 433- 6-Chloro-3- A-30 H represents a 433 1~433- pyridyl combination of 710 substituents corresponding to each row of Table B Table 434- 4-Chloro-3- A-31 H represents a 434 1~434- pyridyl combination of 710 substituents corresponding to each row of Table B Table 435- 2-Chloro-4- A-32 H represents a 435 1~435- pyridyl combination of 710 substituents corresponding to each row of Table B Table 436- 3-Chloro-4- A-33 H represents a 436 1~436- pyridyl combination of 710 substituents corresponding to each row of Table B Table 437- 3-bromo-2- A-34 H represents a 437 1~437- pyridyl combination of 710 substituents corresponding to each row of Table B Table 438- 4-bromo-2- A-35 H represents a 438 1~438- pyridyl combination of 710 substituents corresponding to each row of Table B Table 439- 2-FIuoro-4- A-36 H represents a 439 1~439- pyridyl combination of 710 substituents corresponding to each row of Table B Table 440- 3-Fluoro-4- A-37 H represents a 440 1~440- pyridyl combination of 710 substituents corresponding to each row of Table B Table 441- 6-Fluoro-3- A-38 H represents a 441 1~441- pyridyl combination of 710 substituents corresponding to each row of Table B Table 442- 3-iodo-2- A-39 H represents a 442 1~442- pyridyl combination of 710 substituents corresponding to each row of Table B Table 443- 6-Fluoro-3- A-40 H represents a 443 1~443- pyridyl combination of 710 substituents corresponding to each row of Table B Table 444- 2-Chloro-5- A-38 H represents a 444 1~444- thiazolyl combination of 710 substituents corresponding to each row of Table B

TABLE 15 Table A Compound No. Ar A Y R Table 445- 6-Chloro-3- A-1 3- represents a 445 1~445- pyridyl CH3 combination of 710 substituents corresponding to each row of Table B Table 446- 2-Chloro-5- A-1 3- represents a 446 1~446- thiazolyl CH3 combination of 710 substituents corresponding to each row of Table B Table 447- 6-Fluoro-3- A-1 3- represents a 447 1~447- pyridyl CH3 combination of 710 substituents corresponding to each row of Table B Table 448- 6-Bromo-3- A-1 3- represents a 448 1~448- pyridyl CH3 combination of 710 substituents corresponding to each row of Table B Table 449- 6-Chloro-5- A-1 3- represents a 449 1~449- fluoro-3- CH3 combination of 710 pyridyl substituents corresponding to each row of Table B Table 450- 2-Chloro-5- A-1 3- represents a 450 1~450- pyrimidinyl CH3 combination of 710 substituents corresponding to each row of Table B Table 451- 5- A-1 3- represents a 451 1~451- Chloro- CH3 combination of 710 pyrazin-2-yl substituents corresponding to each row of Table B Table 452- 6- A-1 3- represents a 452 1~452- Chloro- CH3 combination of 710 pyridazin-3-yl substituents corresponding to each row of Table B Table 453- 2-Chloro-5- A-1 3- represents a 453 1~453- oxazolyl CH3 combination of 710 substituents corresponding to each row of Table B Table 454- 6- A-1 3- represents a 454 1~454- trifluoromethyl-3- CH3 combination of 710 pyridyl substituents corresponding to each row of Table B Table 455- 3- A-1 3- represents a 455 1~455- tetrahydro- CH3 combination of 710 furanyl substituents corresponding to each row of Table B Table 456- 6-Chloro-3- A-1 4- represents a 456 1~456- pyridyl CH3 combination of 710 substituents corresponding to each row of Table B Table 457- 2-Chloro-5- A-1 4- represents a 457 1~457- thiazolyl CH3 combination of 710 substituents corresponding to each row of Table B Table 458- 6-Fluoro-3- A-1 4- represents a 458 1~458- pyridyl CH3 combination of 710 substituents corresponding to each row of Table B Table 459- 6-Bromo-3- A-1 4- represents a 459 1~459- pyridyl CH3 combination of 710 substituents corresponding to each row of Table B Table 460- 6-Chloro-5- A-1 4- represents a 460 1~460- Fluoro-3- CH3 combination of 710 pyridyl substituents corresponding to each row of Table B Table 461- 2-Chloro-5- A-1 4- represents a 461 1~461- pyrimidinyl CH3 combination of 710 substituents corresponding to each row of Table B Table 462- 5- A-1 4- represents a 462 1~462- Chloro- CH3 combination of 710 pyrazin-2-yl substituents corresponding to each row of Table B Table 463- 6- A-1 4- represents a 463 1~463- Chloro- CH3 combination of 710 pyridazin-3-yl substituents corresponding to each row of Table B Table 464- 2-Chloro-5- A-1 4- represents a 464 1~464- oxazolyl CH3 combination of 710 substituents corresponding to each row of Table B Table 465- 6- A-1 4- represents a 465 1~465- trifluoromethyl-3- CH3 combination of 710 pyridyl substituents corresponding to each row of Table B Table 466- 3- A-1 4- represents a 466 1~466- tetrahydro- CH3 combination of 710 furanyl substituents corresponding to each row of Table B Table 467- 6-Chloro-3- A-1 5- represents a 467 1~467- pyridyl CH3 combination of 710 substituents corresponding to each row of Table B Table 468- 2-Chloro-5- A-1 5- represents a 468 1~468- thiazolyl CH3 combination of 710 substituents corresponding to each row of Table B Table 469- 6-Fluoro-3- A-1 5- represents a 469 1~469- pyridyl CH3 combination of 710 substituents corresponding to each row of Table B Table 470- 6-Bromo-3- A-1 5- represents a 470 1~470- pyridyl CH3 combination of 710 substituents corresponding to each row of Table B Table 471- 6-Chloro-5- A-1 5- represents a 471 1~471- fluoro-3- CH3 combination of 710 pyridyl substituents corresponding to each row of Table B Table 472- 2-Chloro-5- A-1 5- represents a 472 1~472- pyrimidinyl CH3 combination of 710 substituents corresponding to each row of Table B Table 473- 5- A-1 5- represents a 473 1~473- Chloro- CH3 combination of 710 pyrazin-2-yl substituents corresponding to each row of Table B Table 474- 6- A-1 5- represents a 474 1~474- Chloro- CH3 combination of 710 pyridazin-3-yl substituents corresponding to each row of Table B Table 475- 2-Chloro-5- A-1 5- represents a 475 1~475- oxazolyl CH3 combination of 710 substituents corresponding to each row of Table B Table 476- 6- A-1 5- represents a 476 1~476- trifluoro- CH3 combination of 710 methyl-3- substituents pyridyl corresponding to each row of Table B

TABLE 16 Table A Compound No. Ar A Y R Table 477- 3- A-1 5- represents a 477 1~477- tetrahydrofuranyl CH3 combination of 710 substituents corresponding to each row of Table B Table 478- 6-Chloro-3- A-1 6- represents a 478 1~478- pyridyl CH3 combination of 710 substituents corresponding to each row of Table B Table 479- 2-Chloro-5- A-1 6- represents a 479 1~479- thiazolyl CH3 combination of 710 substituents corresponding to each row of Table B Table 480- 6-Fluoro-3- A-1 6- represents a 480 1~480- pyridyl CH3 combination of 710 substituents corresponding to each row of Table B Table 481- 6-Bromo-3- A-1 6- represents a 481 1~481- pyridyl CH3 combination of 710 substituents corresponding to each row of Table B Table 482- 6-Chloro-5- A-1 6- represents a 482 1~482- fluoro-3- CH3 combination of 710 pyridyl substituents corresponding to each row of Table B Table 483- 2-Chloro-5- A-1 6- represents a 483 1~483- pyrimidinyl CH3 combination of 710 substituents corresponding to each row of Table B Table 484- 5- A-1 6 - represents a 484 1~484- Chloropyrazin- CH3 combination of 710 2-yl substituents corresponding to each row of Table B Table 485- 6- A-1 6 - represents a 485 1~485- Chloropyridazin- CH3 combination of 710 3-yl substituents corresponding to each row of Table B Table 486- 2-Chloro-5- A-1 6 - represents a 486 1~486- oxazolyl CH3 combination of 710 substituents corresponding to each row of Table B Table 487- 6- A-1 6 - represents a 487 1~487- trifluoromethyl- CH3 combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 488- 3- A-1 6- represents a 488 1~488- tetrahydrofuranyl CH3 combination of 710 substituents corresponding to each row of Table B Table 489- 6-Chloro-3- A-1 3- represents a 489 1~489- pyridyl NO2 combination of 710 substituents corresponding to each row of Table B Table 490- 2-Chloro-5- A-1 3- represents a 490 1~490- thiazolyl NO2 combination of 710 substituents corresponding to each row of Table B Table 491- 6-Fluoro-3- A-1 3- represents a 491 1~491- pyridyl NO2 combination of 710 substituents corresponding to each row of Table B Table 492- 6-Bromo-3- A-1 3- represents a 492 1~492- pyridyl NO2 combination of 710 substituents corresponding to each row of Table B Table 493- 6-Chloro-5- A-1 3- represents a 493 1~493- Fluoro-3- NO2 combination of 710 pyridyl substituents corresponding to each row of Table B Table 494- 2-Chloro-5- A-1 3- represents a 494 1~494- pyrimidinyl NO2 combination of 710 substituents corresponding to each row of Table B Table 495- 5- A-1 3- represents a 495 1~495- Chloropyrazin- NO2 combination of 710 2-yl substituents corresponding to each row of Table B Table 496- 6- A-1 3- represents a 496 1~496- Chloropyridazin- NO2 combination of 710 3-yl substituents corresponding to each row of Table B Table 497- 2-Chloro-5- A-1 3- represents a 497 1~497- oxazolyl NO2 combination of 710 substituents corresponding to each row of Table B Table 498- 6- A-1 3- represents a 498 1~498- trifluoromethyl- NO2 combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 499- 3- A-1 3- represents a 499 1~499- tetrahydrofuranyl NO2 combination of 710 substituents corresponding to each row of Table B Table 500- 6-Chloro-3- A-1 4- represents a 500 1~500- pyridyl NO2 combination of 710 substituents corresponding to each row of Table B Table 501- 2-Chloro-5- A-1 4- represents a 501 1~501- thiazolyl NO2 combination of 710 substituents corresponding to each row of Table B Table 502- 6-Fluoro-3- A-1 4- represents a 502 1~502- pyridyl NO2 combination of 710 substituents corresponding to each row of Table B Table 503- 6-Bromo-3- A-1 4- represents a 503 1~503- pyridyl NO2 combination of 710 substituents corresponding to each row of Table B Table 504- 6-Chloro-5- A-1 4- represents a 504 1~504- fluoro-3- NO2 combination of 710 pyridyl substituents corresponding to each row of Table B Table 505- 2-Chloro-5- A-1 4- represents a 505 1~505- pyrimidinyl NO2 combination of 710 substituents corresponding to each row of Table B Table 506- 5- A-1 4- represents a 506 1~506- Chloropyrazin- NO2 combination of 710 2-yl substituents corresponding to each row of Table B Table 507- 6- A-1 4- represents a 507 1~507- Chloropyridazin- NO2 combination of 710 3-yl substituents corresponding to each row of Table B Table 508- 2-Chloro-5- A-1 4- represents a 508 1~508- oxazolyl NO2 combination of 710 substituents corresponding to each row of Table B

TABLE 17 Table A Compound No. Ar A Y R Table 509- 6- A-1 4- represents a 509 1~509- trifluoromethyl- NO2 combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 510- 3- A-1 4- represents a 510 1~510- tetrahydrofuranyl NO2 combination of 710 substituents corresponding to each row of Table B Table 511- 6-Chloro-3- A-1 5- represents a 511 1~511- pyridyl NO2 combination of 710 substituents corresponding to each row of Table B Table 512- 2-Chloro-5- A-1 5- represents a 512 1~512- thiazolyl NO2 combination of 710 substituents corresponding to each row of Table B Table 513- 6-Fluoro-3- A-1 5- represents a 513 1~513- pyridyl NO2 combination of 710 substituents corresponding to each row of Table B Table 514- 6-Bromo-3- A-1 5- represents a 514 1~514- pyridyl NO2 combination of 710 substituents corresponding to each row of Table B Table 515- 6-Chloro-5- A-1 5- represents a 515 1~515- fluoro-3- NO2 combination of 710 pyridyl substituents corresponding to each row of Table B Table 516- 2-Chloro-5- A-1 5- represents a 516 1~516- pyrimidinyl NO2 combination of 710 substituents corresponding to each row of Table B Table 517- 5- A-1 5- represents a 517 1~517- Chloropyrazin- NO2 combination of 710 2-yl substituents corresponding to each row of Table B Table 518- 6- A-1 5- represents a 518 1~518- Chloropyridazin- NO2 combination of 710 3-yl substituents corresponding to each row of Table B Table 519- 2-Chloro-5- A-1 5- represents a 519 1~519- oxazolyl NO2 combination of 710 substituents corresponding to each row of Table B Table 520- 6- A-1 5- represents a 520 1~520- trifluoromethyl- NO2 combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 521- 3- A-1 5- represents a 521 1~521- tetrahydrofuranyl NO2 combination of 710 substituents corresponding to each row of Table B Table 522- 6-Chloro-3- A-1 6- represents a 522 1~522- pyridyl NO2 combination of 710 substituents corresponding to each row of Table B Table 523- 2-Chloro-5- A-1 6- represents a 523 1~523- thiazolyl NO2 combination of 710 substituents corresponding to each row of Table B Table 524- 6-Fluoro-3- A-1 6- represents a 524 1~524- pyridyl NO2 combination of 710 substituents corresponding to each row of Table B Table 525- 6-Bromo-3- A-1 6- represents a 525 1~525- pyridyl NO2 combination of 710 substituents corresponding to each row of Table B Table 526- 6-Chloro-5- A-1 6- represents a 526 1~526- Fluoro-3- NO2 combination of 710 pyridyl substituents corresponding to each row of Table B Table 527- 2-Chloro-5- A-1 6- represents a 527 1~527- pyrimidinyl NO2 combination of 710 substituents corresponding to each row of Table B Table 528- 5- A-1 6- represents a 528 1~528- Chloropyrazin- NO2 combination of 710 2-yl substituents corresponding to each row of Table B Table 529- 6- A-1 6- represents a 529 1~529- Chloropyridazin- NO2 combination of 710 3-yl substituents corresponding to each row of Table B Table 530- 2-Chloro-5- A-1 6- represents a 530 1~530- oxazolyl NO2 combination of 710 substituents corresponding to each row of Table B Table 531- 6- A-1 6- represents a 531 1~531- trifluoromethyl- NO2 combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 532- 3- A-1 6- represents a 532 1~532- tetrahydrofuranyl NO2 combination of 710 substituents corresponding to each row of Table B Table 533- 6-Chloro-3- A-1 3- represents a 533 1~533- pyridyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 534- 2-Chloro-5- A-1 3- represents a 534 1~534- thiazolyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 535- 6-Fluoro-3- A-1 3- represents a 535 1~535- pyridyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 536- 6-Bromo-3- A-1 3- represents a 536 1~536- pyridyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 537- 6-Chloro-5- A-1 3- represents a 537 1~537- fluoro-3- OCH3 combination of 710 pyridyl substituents corresponding to each row of Table B Table 538- 2-Chloro-5- A-1 3- represents a 538 1~538- pyrimidinyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 539- 5- A-1 3- represents a 539 1~539- Chloropyrazin- OCH3 combination of 710 2-yl substituents corresponding to each row of Table B Table 540- 6- A-1 3- represents a 540 1~540- Chloropyridazin- OCH3 combination of 710 3-yl substituents corresponding to each row of Table B

TABLE 18 Table A Compound No. Ar A Y R Table 541- 2-Chloro-5- A-1 3- represents a 541 1~541- oxazolyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 542- 6- A-1 3- represents a 542 1~542- trifluoromethyl- OCH3 combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 543- 3- A-1 3- represents a 543 1~543- tetrahydrofuranyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 544- 6-Chloro-3- A-1 4- represents a 544 1~544- pyridyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 545- 2-Chloro-5- A-1 4- represents a 545 1~545- thiazolyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 546- 6-Fluoro-3- A-1 4- represents a 546 1~546- pyridyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 547- 6-Bromo-3- A-1 4- represents a 547 1~547- pyridyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 548- 6-Chloro-5- A-1 4- represents a 548 1~548- Fluoro-3- OCH3 combination of 710 pyridyl substituents corresponding to each row of Table B Table 549- 2-Chloro-5- A-1 4- represents a 549 1~549- pyrimidinyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 550- 5- A-1 4- represents a 550 1~550- Chloropyrazin- OCH3 combination of 710 2-yl substituents corresponding to each row of Table B Table 551- 6- A-1 4- represents a 551 1~551- Chloropyridazin- OCH3 combination of 710 3-yl substituents corresponding to each row of Table B Table 552- 2-Chloro-5- A-1 4- represents a 552 1~552- oxazolyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 553- 6- A-1 4- represents a 553 1~553- trifluoromethyl- OCH3 combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 554- 3- A-1 4- represents a 554 1~554- tetrahydrofuranyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 555- 6-Chloro-3- A-1 5- represents a 555 1~555- pyridyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 556- 2-Chloro-5- A-1 5- represents a 556 1~556- thiazolyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 557- 6-Fluoro-3- A-1 5- represents a 557 1~557- pyridyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 558- 6-Bromo-3- A-1 5- represents a 558 1~558- pyridyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 559- 6-Chloro-5- A-1 5- represents a 559 1~559- fluoro-3- OCH3 combination of 710 pyridyl substituents corresponding to each row of Table B Table 560- 2-Chloro-5- A-1 5- represents a 560 1~560- pyrimidinyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 561- 5- A-1 5- represents a 561 1~561- Chloropyrazin- OCH3 combination of 710 2-yl substituents corresponding to each row of Table B Table 562- 6- A-1 5- represents a 562 1~562- Chloropyridazin- OCH3 combination of 710 3-yl substituents corresponding to each row of Table B Table 563- 2-Chloro-5- A-1 5- represents a 563 1~563- oxazolyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 564- 6- A-1 5- represents a 564 1~564- trifluoromethyl- OCH3 combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 565- 3- A-1 5- represents a 565 1~565- tetrahydrofuranyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 566- 6-Chloro-3- A-1 6 - represents a 566 1~566- pyridyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 567- 2-Chloro-5- A-1 6 - represents a 567 1~567- thiazolyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 568- 6-Fluoro-3- A-1 6 - represents a 568 1~568- pyridyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 569- 6-Bromo-3- A-1 6 - represents a 569 1~569- pyridyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 570- 6-Chloro-5- A-1 6 - represents a 570 1~570- Fluoro-3- OCH3 combination of 710 pyridyl substituents corresponding to each row of Table B Table 571- 2-Chloro-5- A-1 6 - represents a 571 1~571- pyrimidinyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 572- 5- A-1 6- represents a 572 1~572- Chloropyrazin- OCH3 combination of 710 2-yl substituents corresponding to each row of Table B

TABLE 19 Table A Compound No. Ar A Y R Table 573- 6- A-1 6- represents a 573 1~573- Chloropyridazin- OCH3 combination of 710 3-yl substituents corresponding to each row of Table B Table 574- 2-Chloro-5- A-1 6- represents a 574 1~574- oxazolyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 575- 6- A-1 6- represents a 575 1~575- trifluoromethyl- OCH3 combination of 710 3-pyridyl substituents corresponding to each row of Table B Table 576- 3- A-1 6- represents a 576 1~576- tetrahydrofuranyl OCH3 combination of 710 substituents corresponding to each row of Table B Table 577- 2,6- A-1 H represents a 577 1~577- dichloro-3- combination of 710 pyridyl substituents corresponding to each row of Table B Table 578- 3-pyridyl A-1 H represents a 578 1~578- combination of 710 substituents corresponding to each row of Table B Table 579- 4-pyridyl A-1 H represents a 579 1~579- combination of 710 substituents corresponding to each row of Table B Table 580- 6-chloro-3- A-1 H represents a 580 1~580- pyridyl-N- combination of 710 oxide substituents corresponding to each row of Table B

TABLE B R

    R1 1 H 2 CF3 3 CHF2 4 CF2Cl 5 CF2CF3 6 CH2Cl 7 CHCl2 8 CCl3 9 CHClBr 10 2,2- difluorocyclopropyl 11 2,3,3- trifluoroacryl 12 CH2CHF2 13 CH2CF3 14 CH═CH2 15 CH2C≡CH 16 CH2CH2C≡CH

    R2 17 CH2CF3 18 CH(Me)CF3 19 CH(CF3)2

    R3 20 CF3 21 CHF2 22 CF2Cl 23 CF2CF3 24 CH2Cl 25 CHCl2 26 CCl3 27 CHClBr 28 CHBr2 29 2,3,3- trifluoroacryl 30 CH2CHF2 31 CH2CF3 32 CH═CH2 33 CH2C≡CH 34 CH2CF3 35 CH2CH2Ph 36 Me 37 Et 38 n-Pr 39 i-Pr 40 cyclopropyl R

R4 R5 41 H CF3 42 Me CF3 43 Et CF3 44 n-Pr CF3 45 i-Pr CF3 46 t-Bu CF3 47 n-Bu CF3 48 n-Pentyl CF3 49 n-Hexyl CF3 50 cyclopropyl CF3 51 cyclobutyl CF3 52 cyclopentyl CF3 53 cyclohexyl CF3 54 CH═CH2 CF3 55 CH2CH═CH2 CF3 56 CH2C≡CH CF3 57 CH2CH2C 

 CH CF3 58 CH2CHF2 CF3 59 CH2CCF3 CF3 60 CH2CH2Cl CF3 61 CH2CHCl2 CF3 62 2-fluoro-2- CF3 chloroethyl 63 CH2CCl3 CF3 64 CH2CN CF3 65 CH2CH2CN CF3 66 CH2CH(CN)CH2CN CF3 67 CH2CH2OH CF3 68 CH2CH2HC2OH CF3 69 CH2CH(OH)CH2OH CF3 70 CH2CH2NO2 CF3 71 Phenyl CF3 72 CH2-Phenyl CF3 73 CH(Me)-Phenyl CF3 74 C(Me2)-Phenyl CF3 75 C(cyclopropyl)- CF3 Phenyl 76 CH2CH2-Phenyl CF3 77 CH2-(2- CF3 Methylphenyl) 78 CH2-(3- CF3 Methylphenyl) 79 CH2-(4- CF3 Methylphenyl) 80 CH2-(2- CF3 Methoxylphenyl) 81 CH2-(3- CF3 Methoxylphenyl) 82 CH2-(4- CF3 Methoxylphenyl) 83 CH2-(2- CF3 fluorolphenyl) 84 CH2-(3- CF3 fluorolphenyl) 85 CH2-(4- CF3 fluorolphenyl) 86 CH2-(2- Chlorophenyl) 87 CH2-(3- CF3 Chlorophenyl) 88 CH2-(4- CF3 Chlorophenyl) 89 CH2-(2- CF3 Bromophenyl) 90 CH2-(3- CF3 Bromophenyl) 91 CH2-(4- CF3 Bromophenyl) 92 CH2-(2- CF3 iodophenyl) 93 CH2-(3- CF3 iodophenyl) 94 CH2-(4- CF3 iodophenyl) 95 CH2-(1- CF3 naphthalenyl) 96 CH2-(2- CF3 naphthalenyl) 97 naphthalen-1- CF3 ylmethyl 98 naphthalen-2- CF3 ylmethyl 99 quinolin-2- CF3 ylmethyl 100 quinolin-7- CF3 ylmethyl 101 isoquinolin- CF3 7-ylmethyl 102 isoquinolin- CF3 6-ylmethyl 103 quinolin-6- CF3 ylmethyl 104 quinolin-3- CF3 ylmethyl 105 isoquinolin- CF3 3-ylmethyl 106 isoquinolin- CF3 1-ylmethyl 107 isoquinolin- CF3 4-ylmethyl 108 quinolin-4- CF3 ylmethyl 109 quinolin-5- CF3 ylmethyl 110 isoquinolin- CF3 5-ylmethyl 111 isoquinolin- CF3 8-ylmethyl 112 quinolin-8- CF3 ylmethyl 113 CH2O-Phenyl CF3 114 CH2CH2O-Phenyl CF3 115 2-pyridyl CF3 116 3-pyridyl CF3 117 4-pyridyl CF3 118 CH2-(2- CF3 pyridyl) 119 CH2-(3- CF3 pyridyl) 120 CH2-(4-Chloro- CF3 3-pyridyl) 121 CH2-(4- CF3 pyridyl) 122 CH2-(2- CF3 thienyl) 123 CH2-(3- CF3 thienyl) 124 CH2-(2- CF3 furanyl) 125 CH2-(3- CF3 furanyl) 126 CH2-(2- CF3 tetrahydrofuranyl) 127 CH2-(3- CF3 tetrahydrofuranyl) 128 (1H-imidazol-2- CF3 yl)methyl 129 (1H-imidazol-1- CF3 yl)methyl 130 (1H-imidazol-4- CF3 yl)methyl 131 CH2-(2- CF3 thiazolyl) 132 CH2-(3- CF3 thiazolyl) 133 CH2-(2-pyrrolyl) CF3 134 CH2-(3-pyrrolyl) CF3 135 CH2-(5- CF3 methylpyrazol-1-yl) 136 CH2-(1- CF3 pyrazolyl) 137 CH2-(2- CF3 pyrazolyl) 138 CH2-(3- CF3 pyrazolyl) 139 CH2-(4- CF3 pyrazolyl) 140 CH2-(5- CF3 pyrazolyl) 141 CH2-(2- CF3 oxazolyl) 142 CH2-(3- CF3 oxazolyl) 143 CH2-(3- CF3 isoxazolyl) 144 CH2-(4- CF3 isoxazolyl) 145 CH2-(5- CF3 isoxazolyl) 146 CH2CH2OCH3 CF3 147 CH2CH2OCH2CH3 CF3 148 CH2CH2CH2OCH3 CF3 149 CH2CH2CH2OCH2CH3 CF3 150 CH2CH2SCH3 CF3 151 CH2CH2SCH2CH3 CF3 152 CH2CH2CH2SCH3 CF3 153 CH2CH2CH2SCH2CH3 CF3 154 Me CHF2 155 Et CHF2 156 n-Pr CHF2 157 i-Pr CHF2 158 t-Bu CHF2 159 n-Bu CHF2 160 n-Pentyl CHF2 161 n-Hexyl CHF2 162 cyclopropyl CHF2 163 cyclobutyl CHF2 164 cyclopentyl CHF2 165 cyclohexyl CHF2 166 CH═CH2 CHF2 167 CH2CH═CH2 CHF2 168 CH2C≡CH CHF2 169 CH2CH2C≡CH CHF2 170 CH2CHF2 CHF2 171 CH2CCF3 CHF2 172 CH2CH2Cl CHF2 173 CH2CHCl2 CHF2 174 2-fluoro-2- CHF2 chloroethyl 175 CH2CCl3 CHF2 176 CH2CH2CN CHF2 177 CH2CH2CH2CN CHF2 178 CH2CH(CN)CH2CN CHF2 179 CH2CH2OH CHF2 180 CH2CH2CH2OH CHF2 181 CH2CH(OH)CH2OH CHF2 182 CH2CH2NO2 CHF2 183 Phenyl CHF2 184 CH2-Phenyl CHF2 185 CH(Me)-Phenyl CHF2 186 C(Me2)-Phenyl CHF2 187 C(cyclopropyl)- CHF2 Phenyl 188 CH2CH2-Phenyl CHF2 189 CH2-(2- CHF2 Methylphenyl) 190 CH2-(3- CHF2 Methylphenyl) 191 CH2-(4- CHF2 Methylphenyl) 192 CH2-(2- CHF2 Methoxylphenyl) 193 CH2-(3- CHF2 Methoxylphenyl) 194 CH2-(4- CHF2 Methoxylphenyl) 195 CH2-(2- CHF2 fluorolphenyl) 196 CH2-(3- CHF2 fluorolphenyl) 197 CH2-(4- CHF2 fluorolphenyl) 198 CH2-(2- CHF2 Chlorophenyl) 199 CH2-(3- CHF2 Chlorophenyl) 200 CH2-(4- CHF2 Chlorophenyl) 201 CH2-(2- CHF2 Bromophenyl) 202 CH2-(3- CHF2 Bromophenyl) 203 CH2-(4- CHF2 Bromophenyl) 204 CH2-(2- CHF2 iodophenyl) 205 CH2-(3- CHF2 iodophenyl) 206 CH2-(4- CHF2 iodophenyl) 207 CH2-(1- CHF2 naphthalenyl) 208 CH2-(2- CHF2 naphthalenyl) 209 naphthalen-1- CHF2 ylmethyl 210 naphthalen-2- CHF2 ylmethyl 211 quinolin-2- CHF2 ylmethyl 212 quinolin-7- CHF2 ylmethyl 213 isoquinolin- CHF2 7-ylmethyl 214 isoquinolin- CHF2 6-ylmethyl 215 quinolin-6- CHF2 ylmethyl 216 quinolin-3- CHF2 ylmethyl 217 isoquinolin- CHF2 3-ylmethyl 218 isoquinolin- CHF2 1-ylmethyl 219 isoquinolin- CHF2 4-ylmethyl 220 quinolin-4- CHF2 ylmethyl 221 quinolin-5- CHF2 ylmethyl 222 isoquinolin- CHF2 5-ylmethyl 223 isoquinolin- CHF2 8-ylmethyl 224 quinolin-8- CHF2 ylmethyl 225 CH2O-Phenyl CHF2 226 CH2CH2O-Phenyl CHF2 227 2-pyridyl CHF2 228 3-pyridyl CHF2 229 4-pyridyl CHF2 230 CH2-(2- CHF2 pyridyl) 231 CH2-(3- CHF2 pyridyl) 232 CH2-(4- CHF2 Chloro-3- pyridyl) 233 CH2-(4- CHF2 pyridyl) 234 CH2-(2- CHF2 thienyl) 235 CH2-(3-thienyl) CHF2 236 CH2-(2-furanyl) CHF2 237 CH2-(3-furanyl) CHF2 238 CH2-(2- CHF2 tetrahydrofuranyl) 239 CH2-(3- CHF2 tetrahydrofuranyl) 240 (1H-imidazol-2- CHF2 yl)methyl 241 (1H-imidazol-1- CHF2 yl)methyl 242 (1H-imidazol-4- CHF2 yl)methyl 243 CH2-(2- CHF2 thiazolyl) 244 CH2-(3- CHF2 thiazolyl) 245 CH2-(2-pyrrolyl) CHF2 246 CH2-(3- CHF2 pyrrolyl) 247 CH2-(5- CHF2 methylpyrazol-1-yl) 248 CH2-(1- CHF2 pyrazolyl) 249 CH2-(2- CHF2 pyrazolyl) 250 CH2-(3- CHF2 pyrazolyl) 251 CH2-(4- CHF2 pyrazolyl) 252 CH2-(5- CHF2 pyrazolyl) 253 CH2-(2- CHF2 oxazolyl) 254 CH2-(3- CHF2 oxazolyl 255 CH2-(3- CHF2 isoxazolyl) 256 CH2-(4- CHF2 isoxazolyl) 257 CH2-(5- CHF2 isoxazolyl) 258 CH2CH2OCH3 CHF2 259 CH2CH2OCH2CH3 CHF2 260 CH2CH2CH2OCH3 CHF2 261 CH2CH2CH2OCH2CH3 CHF2 262 CH2CH2SCH3 CHF2 263 CH2CH2SCH2CH3 CHF2 264 CH2CH2CH2SCH3 CHF2 265 CH2CH2CH2SCH2CH3 CHF2 266 Me CF2Cl 267 Et CF2Cl 268 n-Pr CF2Cl 269 i-Pr CF2Cl 270 t-Bu CF2Cl 271 n-Bu CF2Cl 272 n-Pentyl CF2Cl 273 n-Hexyl CF2Cl 274 cyclopropyl CF2Cl 275 cyclobutyl CF2Cl 276 cyclopentyl CF2Cl 277 cyclohexyl CF2Cl 278 CH═CH2 CF2Cl 279 CH2CH═CH2 CF2Cl 280 CH2C≡CH CF2Cl 281 CH2CH2C≡CH CF2Cl 282 CH2CHF2 CF2Cl 283 CH2CCF3 CF2Cl 284 CH2CH2Cl CF2Cl 285 CH2CHCl2 CF2Cl 286 2-fluoro-2- CF2Cl chloroethyl 287 CH2CCl3 CF2Cl 288 CH2CH2CN CF2Cl 289 CH2CH2CH2CN CF2Cl 290 CH2CH(CN)CH2CN CF2Cl 291 CH2CH2OH CF2Cl 292 CH2CH2CH2OH CF2Cl 293 CH2CH(OH)CH2OH CF2Cl 294 CH2CH2NO2 CF2Cl 295 Phenyl CF2Cl 296 CH2-Phenyl CF2Cl 297 CH(Me)-Phenyl CF2Cl 298 C(Me2)-Phenyl CF2Cl 299 C(cyclopropyl)- CF2Cl Phenyl 300 CH2CH2-Phenyl CF2Cl 301 CH2-(2- CF2Cl Methylphenyl) 302 CH2-(3- CF2Cl Methylphenyl) 303 CH2-(4- CF2Cl Methylphenyl) 304 CH2-(2- CF2Cl Methoxylphenyl) 305 CH2-(3- CF2Cl Methoxylphenyl) 306 CH2-(4- CF2Cl Methoxylphenyl) 307 CH2-(2- CF2Cl fluorolphenyl) 308 CH2-(3- CF2Cl fluorolphenyl) 309 CH2-(4- CF2Cl fluorolphenyl) 310 CH2-(2- CF2Cl Chlorophenyl) 311 CH2-(3- CF2Cl Chlorophenyl) 312 CH2-(4- CF2Cl Chlorophenyl) 313 CH2-(2- CF2Cl Bromophenyl) 314 CH2-(3- CF2Cl Bromophenyl) 315 CH2-(4- CF2Cl Bromophenyl) 316 CH2-(2- CF2Cl iodophenyl) 317 CH2-(3- CF2Cl iodophenyl) 318 CH2-(4- CF2Cl iodophenyl) 319 CH2-(1- CF2Cl naphthalenyl) 320 CH2-(2- CF2Cl naphthalenyl) 321 naphthalen-1- CF2Cl ylmethyl 322 naphthalen-2- CF2Cl ylmethyl 323 quinolin-2- CF2Cl ylmethyl 324 quinolin-7- CF2Cl ylmethyl 325 isoquinolin- CF2Cl 7-ylmethyl 326 isoquinolin- CF2Cl 6-ylmethyl 327 quinolin-6- CF2Cl ylmethyl 328 quinolin-3- CF2Cl ylmethyl 329 isoquinolin- CF2Cl 3-ylmethyl 330 isoquinolin- CF2Cl 1-ylmethyl 331 isoquinolin- CF2Cl 4-ylmethyl 332 quinolin-4- CF2Cl ylmethyl 333 quinolin-5- CF2Cl ylmethyl 334 isoquinolin- CF2Cl 5-ylmethyl 335 isoquinolin- CF2Cl 8-ylmethyl 336 quinolin-8- CF2Cl ylmethyl 337 CH2O-Phenyl CF2Cl 338 CH2CH2O- CF2Cl Phenyl 339 2-pyridyl CF2Cl 340 3-pyridyl CF2Cl 341 4-pyridyl CF2Cl 342 CH2-(2-pyridyl) CF2Cl 343 CH2-(3-pyridyl) CF2Cl 344 CH2-(4-Chloro-3- CF2Cl pyridyl) 345 CH2-(4-pyridyl) CF2Cl 346 CH2-(2-thienyl) CF2Cl 347 CH2-(3-thienyl) CF2Cl 348 CH2-(2-furanyl) CF2Cl 349 CH2-(3-furanyl) CF2Cl 350 CH2-(2- CF2Cl tetrahydrofuranyl) 351 CH2-(3- CF2Cl tetrahydrofuranyl) 352 (1H-imidazol-2- CF2Cl yl)methyl 353 (1H-imidazol-1- CF2Cl yl)methyl 354 (1H-imidazol-4- CF2Cl yl)methyl 355 CH2-(2- CF2Cl thiazolyl) 356 CH2-(3- CF2Cl thiazolyl) 357 CH2-(2- CF2Cl pyrrolyl) 358 CH2-(3- CF2Cl pyrrolyl) 359 CH2-(1- CF2Cl pyrazolyl) 360 CH2-(2- CF2Cl pyrazolyl) 361 CH2-(3- CF2Cl pyrazolyl) 362 CH2-(4- CF2Cl pyrazolyl) 363 CH2-(5- CF2Cl pyrazolyl) 364 CH2-(5- CF2Cl pyrazolyl) 365 CH2-(2- CF2Cl oxazolyl) 366 CH2-(3- CF2Cl oxazolyl 367 CH2-(3- CF2Cl isoxazolyl) 368 CH2-(4- CF2Cl isoxazolyl) 369 CH2-(5- CF2Cl isoxazolyl) 370 CH2CH2OCH3 CF2Cl 371 CH2CH2OCH2CH3 CF2Cl 372 CH2CH2CH2OCH3 CF2Cl 373 CH2CH2CH2OCH2CH3 CF2Cl 374 CH2CH2SCH3 CF2Cl 375 CH2CH2SCH2CH3 CF2Cl 376 CH2CH2CH2SCH3 CF2Cl 377 CH2CH2CH2SCH2CH3 CF2Cl 378 Me CF2CF3 379 Et CF2CF3 380 n-Pr CF2CF3 381 i-Pr CF2CF3 382 t-Bu CF2CF3 383 n-Bu CF2CF3 384 n-Pentyl CF2CF3 385 n-Hexyl CF2CF3 386 cyclopropyl CF2CF3 387 cyclobutyl CF2CF3 388 cyclopentyl CF2CF3 389 cyclohexyl CF2CF3 390 CH═CH2 CF2CF3 391 CH2CH═CH2 CF2CF3 392 CH2C≡CH CF2CF3 393 CH2CH2C≡CH CF2CF3 394 CH2CHF2 CF2CF3 395 CH2CCF3 CF2CF3 396 CH2CH2Cl CF2CF3 397 CH2CHCl2 CF2CF3 398 2-fluoro-2- CF2CF3 chloroethyl 399 CH2CCl3 CF2CF3 400 CH2CH2CN CF2CF3 401 CH2CH2CH2CN CF2CF3 402 CH2CH(CN)CH2CN CF2CF3 403 CH2CH2OH CF2CF3 404 CH2CH2CH2OH CF2CF3 405 CH2CH(OH)CH2OH CF2CF3 406 CH2CH2NO2 CF2CF3 407 Phenyl CF2CF3 408 CH2-Phenyl CF2CF3 409 CH(Me)-Phenyl CF2CF3 410 C(Me2)-Phenyl CF2CF3 411 C(cyclopropyl)- CF2CF3 Phenyl 412 CH2CH2-Phenyl CF2CF3 413 CH2-(2- CF2CF3 Methylphenyl) 414 CH2-(3- CF2CF3 Methylphenyl) 415 CH2-(4- CF2CF3 Methylphenyl) 416 CH2-(2- CF2CF3 Methoxylphenyl) 417 CH2-(3- CF2CF3 Methoxylphenyl) 418 CH2-(4- CF2CF3 Methoxylphenyl) 419 CH2-(2- CF2CF3 fluorolphenyl) 420 CH2-(3- CF2CF3 fluorolphenyl) 421 CH2-(4- CF2CF3 fluorolphenyl) 422 CH2-(2- CF2CF3 Chlorophenyl) 423 CH2-(3- CF2CF3 Chlorophenyl) 424 CH2-(4- CF2CF3 Chlorophenyl) 425 CH2-(2- CF2CF3 Bromophenyl) 426 CH2-(3- CF2CF3 Bromophenyl) 427 CH2-(4- CF2CF3 Bromophenyl) 428 CH2-(2- CF2CF3 iodophenyl) 429 CH2-(3- CF2CF3 iodophenyl) 430 CH2-(4- CF2CF3 iodophenyl) 431 CH2-(1- CF2CF3 naphthalenyl) 432 CH2-(2- CF2CF3 naphthalenyl) 433 naphthalen-1- CF2CF3 ylmethyl 434 naphthalen-2- CF2CF3 ylmethyl 435 quinolin-2- CF2CF3 ylmethyl 436 quinolin-7- CF2CF3 ylmethyl 437 isoquinolin- CF2CF3 7-ylmethyl 438 isoquinolin- CF2CF3 6-ylmethyl 439 quinolin-6- CF2CF3 ylmethyl 440 quinolin-3- CF2CF3 ylmethyl 441 isoquinolin- CF2CF3 3-ylmethyl 442 isoquinolin- CF2CF3 1-ylmethyl 443 isoquinolin- CF2CF3 4-ylmethyl 444 quinolin-4- CF2CF3 ylmethyl 445 quinolin-5- CF2CF3 ylmethyl 446 isoquinolin- CF2CF3 5-ylmethyl 447 isoquinolin- CF2CF3 8-ylmethyl 448 quinolin-8- CF2CF3 ylmethyl 449 CH2O-Phenyl CF2CF3 450 CH2CH2O-Phenyl CF2CF3 451 2-pyridyl CF2CF3 452 3-pyridyl CF2CF3 453 4-pyridyl CF2CF3 454 CH2-(2-pyridyl) CF2CF3 455 CH2-(3-pyridyl) CF2CF3 456 CH2-(4-Chloro-3- CF2CF3 pyridyl) 457 CH2-(4-pyridyl) CF2CF3 458 CH2-(2-thienyl) CF2CF3 459 CH2-(3-thienyl) CF2CF3 460 CH2-(2-furanyl) CF2CF3 461 CH2-(3-furanyl) CF2CF3 462 CH2-(2- CF2CF3 tetrahydrofuranyl) 463 CH2-(3- CF2CF3 tetrahydrofuranyl) 464 (1H-imidazol-2- CF2CF3 yl)methyl 465 (1H-imidazol-1- CF2CF3 yImethyl 466 (1H-imidazol-4- CF2CF3 yl)methyl 467 CH2-(2- CF2CF3 thiazolyl) 468 CH2-(3- CF2CF3 thiazolyl) 469 CH2-(2- CF2CF3 pyrrolyl) 470 CH2-(3- CF2CF3 pyrrolyl) 471 CH2-(5- CF2CF3 methylpyrazolyl-1-yl) 472 CH2-(1- CF2CF3 pyrazolyl) 473 CH2-(2- CF2CF3 pyrazolyl) 474 CH2-(3- CF2CF3 pyrazolyl) 475 CH2-(4- CF2CF3 pyrazolyl) 476 CH2-(5- CF2CF3 pyrazolyl) 477 CH2-(2- CF2CF3 oxazolyl) 478 CH2-(3- CF2CF3 oxazolyl 479 CH2-(3- CF2CF3 isoxazolyl) 480 CH2-(4- CF2CF3 isoxazolyl) 481 CH2-(5- CF2CF3 isoxazolyl) 482 CH2CH2OCH3 CF2CF3 483 CH2CH2OCH2CH3 CF2CF3 484 CH2CH2CH2OCH3 CF2CF3 485 CH2CH2CH2OCH2CH3 CF2CF3 486 CH2CH2SCH3 CF2CF3 487 CH2CH2SCH2CH3 CF2CF3 488 CH2CH2CH2SCH3 CF2CF3 489 CH2CH2CH2SCH2CH3 CF2CF3 490 Me CF2CF3 491 Et CH2Cl 492 n-Pr CHCl2 493 i-Pr CCl3 494 t-Bu CHClBr 495 n-Bu CHBr2 496 n-Pentyl CH═CH2 497 n-Hexyl CH2CH═CH2 498 cyclopropyl CH2C≡CH

R6 R7 499 H CF3 500 Me CF3 501 Et CF3 502 n-Pr CF3 503 i-Pr CF3 504 t-Bu CF3 505 cyclopropyl CF3 506 CH═CH2 CF3 507 CH2CH═CH2 CF3 508 CH2C≡CH CF3 509 Ph CF3 510 CH2Ph CF3 511 COMe CF3 512 COEt CF3 513 CO-n-Pr CF3 514 CO-i-Pr CF3 515 CO-cyclopropyl CF3 516 COCH═CH2 CF3 517 COCH2CH═CH2 CF3 518 COCH2C≡CH CF3 519 COPh CF3 520 CO-(2-pyridyl) CF3 521 CO-(3-pyridyl) CF3 522 CO-(4-pyridyl) CF3 523 COOMe CF3 524 COOEt CF3 525 COO-i-Pr CF3 526 COO-t-Bu CF3 527 COOPh CF3 528 SO2Me CF3 529 SO2Et CF3 530 SO2Ph CF3 531 SO2-(4- CF3 methylphenyl) 532 NHMe CF3 533 NHEt CF3 534 NH-n-Pr CF3 535 NHCH2CH2Cl CF3 536 NHCH2Ph CF3 537 N(Me)2 CF3 538 Me CHF2 539 Et CHF2 540 n-Pr CHF2 541 i-Pr CHF2 542 t-Bu CHF2 543 cyclopropyl CHF2 544 CH═CH2 CHF2 545 CH2CH═CH2 CHF2 546 CH2C≡CH CHF2 547 Ph CHF2 548 CH2Ph CHF2 549 COMe CHF2 550 COEt CHF2 551 CO-n-Pr CHF2 552 CO-i-Pr CHF2 553 CO-cyclopropyl CHF2 554 COCH═CH2 CHF2 555 COCH2CH═CH2 CHF2 556 COCH2C≡CH CHF2 557 COPh CHF2 558 CO-(2-pyridyl) CHF2 559 CO-(3-pyridyl) CHF2 560 CO-(4-pyridyl) CHF2 561 COOMe CHF2 562 COOEt CHF2 563 COO-i-Pr CHF2 564 COO-t-Bu CHF2 565 COOPh CHF2 566 SO2Me CHF2 567 SO2Et CHF2 568 SO2Ph CHF2 569 SO2-(4- CHF2 methylphenyl) 570 Me CF2Cl 571 Et CF2Cl 572 n-Pr CF2Cl 573 i-Pr CF2Cl 574 t-Bu CF2Cl 575 cyclopropyl CF2Cl 576 CH═CH2 CF2Cl 577 CH2CH═CH2 CF2Cl 578 CH2C≡CH CF2Cl 579 Ph CF2Cl 580 CH2Ph CF2Cl 581 COMe CF2Cl 582 COEt CF2Cl 583 CO-n-Pr CF2Cl 584 CO-i-Pr CF2Cl 585 CO-cyclopropyl CF2Cl 586 COCH═CH2 CF2Cl 587 COCH2CH═CH2 CF2Cl 588 COCH2C≡CH CF2Cl 589 COPh CF2Cl 590 CO-(2-pyridyl) CF2Cl 591 CO-(3-pyridyl) CF2Cl 592 CO-(4-pyridyl) CF2Cl 593 COOMe CF2Cl 594 COOEt CF2Cl 595 COO-i-Pr CF2Cl 596 COO-t-Bu CF2Cl 597 COOPh CF2Cl 598 SO2Me CF2Cl 599 SO2Et CF2Cl 600 SO2Ph CF2Cl 601 SO2-(4- CF2Cl methylphenyl) 602 Me CF2CF3 603 Et CF2CF3 604 n-Pr CF2CF3 605 i-Pr CF2CF3 606 t-Bu CF2CF3 607 cyclopropyl CF2CF3 608 CH═CH2 CF2CF3 609 CH2CH═CH2 CF2CF3 610 CH2C≡CH CF2CF3 611 Ph CF2CF3 612 CH2Ph CF2CF3 613 COMe CF2CF3 614 COEt CF2CF3 615 CO-n-Pr CF2CF3 616 CO-i-Pr CF2CF3 617 CO-cyclopropyl CF2CF3 618 COCH═CH2 CF2CF3 619 COCH2CH═CH2 CF2CF3 620 COCH2C≡CH CF2CF3 621 COPh CF2CF3 622 CO-(2-pyridyl) CF2CF3 623 CO-(3-pyridyl) CF2CF3 624 CO-(4-pyridyl) CF2CF3 625 COOMe CF2CF3 626 COOEt CF2CF3 627 COO-i-Pr CF2CF3 628 COO-t-Bu CF2CF3 629 COOPh CF2CF3 630 SO2Me CF2CF3 631 SO2Et CF2CF3 632 SO2Ph CF2CF3 633 SO2-(4- CF2CF3 methylphenyl) 634 Me CF2CF3 635 Et CH2Cl 636 n-Pr CHCl2 637 i-Pr CCl3 638 t-Bu CHClBr 639 cyclopropyl CHBr2 640 CH═CH2 CH═CH2 641 CH2CH═CH2 CH2CH═CH2 642 CH2C≡CH CH2C≡CH R

R1 643 C6F5 644 CH2OCH2C6H5

R2 645 CH2C6H5 646 isopropyl 647 CH2CH2CH═CH2

R3 648 C6F5 649 CH2OCH2C6H5 R

R4 R5 650 Ethyl CH2CF3 651 n-Propyl CH2CF3 652 iso-Propyl CH2CF3 653 t-Butyl CH2CF3 654 n-Butyl CH2CF3 655 cyclopropyl CH2CF3 656 cyclopentyl CH2CF3 657 cyclohexyl CH2CF3 658 n-hexa decyl CF3 659 n-tridecyl CF3 660 CH(CH3)CH2CH3 CF3 661 CH(CH3)CH2CH2CH3 CF3 662 CH(CH3)-isopropyl CF3 663 1-phenylethyl CF3 664 1,2,3,4- CF3 tetrahydronaphthalen- 1-yl 665 1-(naphthalen-1- CF3 yl)ethyl 666 1-(naphthalen-1- CF3 yl)propyl 667 1-(furan-2- CF3 yl)ethyl 668 3.3-dimethylbutan- CF3 2-yl 669 1-(thiophen-2- CF3 yl)ethyl 670 CH2CH2F CF3 671 n-Octyl CF3 672 n-Octyl CHF2 673 n-Octyl CF2Cl 674 n-Octyl CF2CF3 675 n-Octyl CF2CF3 676 CH(C6H5)2 CF3 677 CH(C6H5)2 CHF2 678 CH(C6H5)2 CF2Cl 679 CH(C6H5)2 CF2CF3 680 CH(C6H5)2 CF2CF3 681 CH(CH2CH3)2 CF3 682 CH(CH2CH3)2 CHF2 683 CH(CH2CH3)2 CF2Cl 684 CH(CH2CH3)2 CF2CF3 685 CH(CH2CH3)2 CF2CF3 686 CH(CH2CH2CH3)2 CF3 687 CH(CH2CH2CH3)2 CHF2 688 CH(CH2CH2CH3)2 CF2Cl 689 CH(CH2CH2CH3)2 CF2CF3 690 CH(CH2CH2CH3)2 CF2CF3 R

Y1 Y2 Ry 691 O O Methyl 692 O O Ethyl 693 O O Propyl 694 O O isopropyl 695 S O Methyl 696 S O Ethyl 697 S O Propyl 698 S O isopropyl 699 S S Methyl 700 S S Ethyl 701 S S Propyl 702 S S isopropyl

n Rz 703 1 CF3 704 1 CF2CF3 705 1 CH2CF3 706 1 Me 707 2 CF3 708 2 CF2CF3 709 2 CH2CF3 710 2 Me

Examples of preferred compounds of Formula (I) include compounds shown in the following Tables.

TABLE 36 Compound No Ar A Y R 266-2   6-Chloro-3- A-38 H COCF3 pyridyl 444-2   2-chloro-5- A-38 H COCF3 thiazolyl 190-2   6-Chloro-3- A-13 H COCF3 pyridyl 201-2   6-Chloro-3- A-14 H COCF3 pyridyl 223-2   6-Chloro-3- A-16 H COCF3 pyridyl 146-2   6-Chloro-3- A-1 3-OH COCF3 pyridyl 224-2   2-chloro-5- A-16 H COCF3 thiazolyl 102-2   6-Chloro-3- A-1 3-CN COCF3 pyridyl 212-2   6-Chloro-3- A-15 H COCF3 pyridyl 1-20 6-Chloro-3- A-1 H CSCF3 pyridyl 12-2  2-Chloro-4- A-1 H COCF3 pyridyl 213-2   2-chloro-5- A-15 H COCF3 thiazolyl 1-17 6-Chloro-3- A-1 H COOCH2CF3 pyridyl 1-18 6-Chloro-3- A-1 H COOCH(Me)CF3 pyridyl 1-19 6-Chloro-3- A-1 H COOCH(CF3)2 pyridyl 7-2  5- A-1 H COCF3 Chloropyrazin- 2-yl 1-13 6-Chloro-3- A-1 H COCH2CF3 pyridyl 168-2   6-Chloro-3- A-1 5-OH COCF3 pyridyl 1-21 6-Chloro-3- A-1 H CSCHF2 pyridyl 3-20 6-Fluoro-3- A-1 H CSCF3 pyridyl 4-20 6-Bromo-3- A-1 H CSCF3 pyridyl 3-3  6-Fluoro-3- A-1 H COCHF2 pyridyl 4-3  6-Bromo-3- A-1 H COCHF2 pyridyl 5-5  6-Chloro-5- A-1 H COCF2CF3 fluoro-3-pyridyl 6-5  2-Chloro-5- A-1 H COCF2CF3 pyrimidinyl 1-22 6-Chloro-3- A-1 H CSCF2Cl pyridyl 1-23 6-Chloro-3- A-1 H CSCF2CF3 pyridyl 5-20 6-Chloro-5- A-1 H CSCF3 fluoro-3-pyridyl 5-3  6-Chloro-5- A-1 H COCHF2 fluoro-3-pyridyl 6-3  2-Chloro-5- A-1 H COCHF2 pyrimidinyl 8-2  6- A-1 H COCF3 Chloropyridazin- 3-yl 5-4  6-Chloro-5- A-1 H COCF2Cl fluoro-3-pyridyl 4-4  6-Bromo-3- A-1 H COCF2Cl pyridyl 6-4  2-Chloro-5- A-1 H COCF2Cl pyrimidinyl 4-5  6-Bromo-3- A-1 H COCF2CF3 pyridyl 2-20 2-chloro-5- A-1 H CSCF3 thiazolyl 10-20  6- A-1 H CSCF3 trifluoromethyl- 3-pyridyl 3-4  6-Fluoro-3- A-1 H COCF2Cl pyridyl 3-5  6-Fluoro-3- A-1 H COCF2CF3 pyridyl 11-20  3-THF A-1 H CSCF3 1-14 6-Chloro-3- A-1 H COCH═CH2 pyridyl 1-37 6-Chloro-3- A-1 H CSEt pyridyl 1-39 6-Chloro-3- A-1 H CS-i-Pr pyridyl 1-40 6-Chloro-3- A-1 H CS-cyclopropyl pyridyl 1-15 6-Chloro-3- A-1 H COCH2CΞCH pyridyl 1-35 6-Chloro-3- A-1 H CSCH2CH2Ph pyridyl  1-501 6-Chloro-3- A-1 H C(═NOEt)CF3 pyridyl  1-499 6-Chloro-3- A-1 H C(═NOH)CF3 pyridyl  1-510 6-Chloro-3- A-1 H C(═NOCH2Ph)CF3 pyridyl  1-511 6-Chloro-3- A-1 H C(═NOCOMe)CF3 pyridyl  1-519 6-Chloro-3- A-1 H C(═NOCOPh)CF3 pyridyl  1-523 6-Chloro-3- A-1 H C(═NOCOOMe)CF3 pyridyl

TABLE 37 Com- pound No Ar A Y R 1-528 6-Chloro-3- A-1 H C(═NOSO2Me)CF3 pyridyl 1-531 6-Chloro-3- A-1 H C(═NOSO2-(4- pyridyl Methylphenyl))CF3 1-507 6-Chloro-3- A-1 H C(═NOCH2CH═CH2)CF3 pyridyl 1-516 6-Chloro-3- A-1 H C(═NOCOCH═CH2)CF3 pyridyl 1-518 6-Chloro-3- A-1 H C(═NOCOCH2C≡CH)CF3 pyridyl 1-527 6-Chloro-3- A-1 H C(═NOCOOPh)CF3 pyridyl 1-521 6-Chloro-3- A-1 H C(═NOCO-3-pyr)CF3 pyridyl 1-43  6-Chloro-3- A-1 H C(═NEt)CF3 pyridyl 1-536 6-Chloro-3- A-1 H C(═NOCONHCH2Ph)CF3 pyridyl 1-42  6-Chloro-3- A-1 H C(═NMe)CF3 pyridyl 1-500 6-Chloro-3- A-1 H C(═NOMe)CF3 pyridyl 1-504 6-Chloro-3- A-1 H C(═NOtBu)CF3 pyridyl 1-534 6-Chloro-3- A-1 H C(═NOCONHnPr)CF3 pyridyl 1-535 6-Chloro-3- A-1 H C(═NOCONHCH2CH2Cl)CF3 pyridyl 1-72  6-Chloro-3- A-1 H C(═NCH2Ph)CF3 pyridyl 1-150 6-Chloro-3- A-1 H C(═NCH2CH2SMe)CF3 pyridyl 1-67  6-Chloro-3- A-1 H C(═NCH2CH2OH) pyridyl 1-515 6-Chloro-3- A-1 H C(═NOCO-cyclopropyl)CF3 pyridyl 1-56  6-Chloro-3- A-1 H C(═NCH2C Ξ CH)CF3 pyridyl 1-512 6-Chloro-3- A-1 H C(═NOCOCH2CH3)CF3 pyridyl 1-514 6-Chloro-3- A-1 H C(═NOCOiPr)CF3 pyridyl 1-50  6-Chloro-3- A-1 H C(═N-cyclopropyl)CF3 pyridyl 1-114 6-Chloro-3- A-1 H C(═NCH2CH2OPh)CF3 pyridyl 1-44  6-Chloro-3- A-1 H C(═N-n-Pr)CF3 pyridyl 1-118 6-Chloro-3- A-1 H C(═NCH2-(2-pyridyl))CF3 pyridyl 1-119 6-Chloro-3- A-1 H C(═NCH2-(3-pyridyl))CF3 pyridyl 1-47  6-Chloro-3- A-1 H C(═N-n-Bu)CF3 pyridyl 1-55  6-Chloro-3- A-1 H C(═N—CH2CH═CH2)CF3 pyridyl 1-122 6-Chloro-3- A-1 H C(═NCH2-(2-thienyl))CF3 pyridyl 1-45  6-Chloro-3- A-1 H C(═N-i-Pr)CF3 pyridyl 1-124 6-Chloro-3- A-1 H C(═NCH2-(2-furanyl))CF3 pyridyl 1-126 6-Chloro-3- A-1 H C(═NCH2-(2- pyridyl tetrahydrofuranyl))CF3 1-64  6-Chloro-3- A-1 H C(═NCH2CN)CF3 pyridyl 1-146 6-Chloro-3- A-1 H C(═NCH2CH2OCH3)CF3 pyridyl 1-52  6-Chloro-3- A-1 H C(═N-cyclopentyl)CF3 pyridyl 1-121 6-Chloro-3- A-1 H C(═NCH2-(4-pyridyl))CF3 pyridyl 1-53  6~Chloro-3- A-1 H C(═N-cyclohexyl)CF3 pyridyl 1-76  6-Chloro-3- A-1 H C(═NCH2CH2Ph)CF3 pyridyl 267-2   6-Chloro-3- A-39 H COCF3 pyridyl 253-2   6-Chloro-3- A-25 H COCF3 pyridyl 251-2   6-Chloro-3- A-23 H COCF3 pyridyl 13-2   3- A-1 H COCF3 Cyanophenyl 1-1  6-Chloro-3- A-1 H CHO pyridyl 1-41  6-Chloro-3- A-1 H C(═NH)CF3 pyridyl

TABLE 38 Compound No. Ar A Y R 1-647 6-Chloro-3-pyridyl A-1 H COOCH2CH2CH═CH2 1-670 6-Chloro-3-pyridyl A-1 H C(═NCH2CH2F)CF3 157-2   6-Chloro-3-pyridyl A-1 4-OH COCF3 1-10  6-Chloro-3-pyridyl A-1 H CO(2,2-difluonocyclopropyl) 580-2   6-chloro-3-pyridyl-N-oxid A-1 H COCF3 1-671 6-Chloro-3-pyridyl A-1 H C(═N(CH2)7CH3)CF3 1-658 6-Chloro-3-pyridyl A-1 H C(═N(CH2)15CH3)CF3 1-659 6-Chloro-3-pyridyl A-1 H C(═N(CH2)11CH3)CF3 1-660 6-Chloro-3-pyridyl A-1 H C(═NCH(CH3)CH2CH3)CF3 1-681 6-Chloro-3-pyridyl A-1 H C(═NCH(CH2CH3)2)CF3 1-686 6-Chloro-3-pyridyl A-1 H C(═NCH(CH2CH2CH3)2)CF3 1-661 6-Chloro-3-pyridyl A-1 H C(═NCH(CH3)CH2CH2CH3)CF3 1-662 6-Chloro-3-pyridyl A-1 H C(═NCH(iso-propyl)CH3)CF3 1-663 6-Chloro-3-pyridyl A-1 H C(═N(1-phenylethyl))CF3 1-664 6-Chloro-3-pyridyl A-1 H C(═N(1,2,3,4-tetrahydronaphthalen-1-yl)CF3 1-665 6-Chloro-3-pyridyl A-1 H C(═N(1-(naphthalen-1-yl)ethyl))CF3 1-666 6-Chloro-3-pyridyl A-1 H C(═N(1-(naphthalen-1-yl)propyl))CF3 1-667 6-Chloro-3-pyridyl A-1 H C(═N(1-(furan-2-yl)ethyl))CF3 1-676 6-Chloro-3-pyridyl A-1 H C(═NCH(C6H5)2)CF3 1-668 6-Chloro-3-pyridyl A-1 H C(═N(3,3-dimethylbutan-2-yl))CF3 47-2   6-Chloro-3-pyridyl A-1 6-F COCF3 91-2   6-Chloro-3-pyridyl A-1 6-Cl COCF3 478-2   6-Chloro-3-pyridyl A-1 6-CH3 COCF3 479-2   2-Chloro-5-thiazolyl A-1 6-CH3 COCF3 1-51  6-Chloro-3-pyridyl A-1 H C(═N-cyclobutyl)CF3 566-2   6-Chloro-3-pyridyl A-1 6-CH3O COCF3 488-2   3-tetrahydrofuranyl A-1 6-CH3 COCF3 511-2   6-Chloro-3-pyridyl A-1 5-NO2 COCF3 1-669 6-Chloro-3-pyridyl A-1 H C(═N(1-(thiophen-2-yl)ethyl))CF3 179-2   6-Chloro-3-pyridyl A-1 6-OH COCF3 (also represents a tautomer) 555-2   6-Chloro-3-pyridyl A-1 5-OCH3 COCF3 577-2   2,6-dichrolo-3-pyridyl A-1 H COCF3 544-2   6-Chloro-3-pyridyl A-1 4-OCH3 COCF3 168-2   6-Chloro-3-pyridyl A-1 5-OH COCF3 1-644 6-Chloro-3-pyridyl A-1 H COCH2OCH2C6H5 578-644  3-pyridyl A-1 H COCH2OCH2C6H5 1-703 6-Chloro-3-pyridyl A-1 H SOCF3 1-707 6-Chloro-3-pyridyl A-1 H SO2CF3 1-706 6-Chloro-3-pyridyl A-1 H SOCH3 1-692 6-Chloro-3-pyridyl A-1 H P(═O)(OEt)2 1-700 6-Chloro-3-pyridyl A-1 H P(═S)(SEt)2 1-701 6-Chloro-3-pyridyl A-1 H P(═S)(S-n-propyl)2 1-702 6-Chloro-3-pyridyl A-1 H P(═S)(S-isopropyl)2 1-646 6-Chloro-3-pyridyl A-1 H COO-iso-Pr 1-645 6-Chloro-3-pyridyl A-1 H COOCH2C6H5 1-643 6-Chloro-3-pyridyl A-1 H COC6F5 2-643 2-Chloro-5-thiazolyl A-1 H COC6F5

TABLE 39

Compound No. Ar R1a Y P212 6-chloro-3- CF3 H pyridyl P213 2-chloro-5- CF3 H thiazolyl P214 6-chloro-3- OCH3 H pyridyl P215 6-chloro-3- CF3 5- pyridyl Cl P216 6-chloro-3- CF3 5- pyridyl F P217 6-chloro-3- CF3 4- pyridyl Cl P218 2-chloro-5- CF3 5- thiazolyl Cl P219 2-chloro-5- CF3 5- thiazolyl F P220 2-chloro-5- CF3 4- thiazolyl Cl P221 6-chloro-3- CF3 3- pyridyl Me P222 6-chloro-3- CF3 4- pyridyl Me P223 6-chloro-3- CF3 5- pyridyl Me P224 phenyl CF3 H P225 4-chlorophenyl CF3 H P226 3-pyridyl CF3 H P227 6-chloro-5- CF3 H fluoro-3-pyridyl P228 6- CF3 H trifluoromethyl- 3-pyridyl P229 6-fluoro-3- CF3 H pyridyl P230 5,6-dichloro-3- CF3 H pyridyl P231 6-bromo-3- CF3 H pyridyl P232 6-chloro-3- CF3 4- pyridyl F P233 6-chloro-3- CF3 3- pyridyl F P234 6-chloro-3- CHCl2 H pyridyl P235 6-chloro-3- CCl3 H pyridyl P236 6-chloro-3- CH2Cl H pyridyl P238 6-chloro-3- CHF2 H pyridyl P239 6-chloro-3- CF2Cl H pyridyl P240 6-chloro-3- CHClBr H pyridyl P241 6-chloro-3- CHBr2 H pyridyl P242 6-chloro-3- CF2CF3 H pyridyl P243 2-chloro-5- CF3 H pyrimidinyl P244 6-chloro-3- CH2Br H pyridyl

Examples of more preferred compounds include

-   N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide     (Compound P212) and -   N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide     (Compound 1-20),     N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide     (Compound 1-45).

In addition, in the present invention, an acid addition salt of a novel iminopyridine derivative represented by Formula (I) (preferably, an agriculturally and zootechnically acceptable acid addition salt) may also be used, and examples thereof include an acid addition salt such as hydrochloride, nitrate, sulfate, phosphate, or acetate and the like.

The novel iminopyridine derivative represented by Formula (I) itself shows excellent pest control effects against pest insects, and is mixed and used with other pest control agents, thereby showing excellent pest control effects compared to when a single agent is used. Therefore, the present invention provides a pest control composition prepared by containing at least one of novel iminopyridine derivatives represented by Formula (I) and at least one of other pest control agents. Furthermore, the present invention provides an excellent pest control composition prepared by containing at least one of novel iminopyridine derivatives represented by Formula (I) and at least one of other insecticides and/or fungicides.

Examples of a pest control composition provided by the present invention include a pest control agent for agricultural and horticultural, a control agent for animal parasitic pests, an agent for controlling hygiene pests, an agent for controlling nuisance pests, an agent for controlling stored grain and stored product pests, an agent for controlling house pests and the like, preferred examples thereof include a pest control agent for agricultural and horticultural and a control agent for animal parasitic pests.

Examples of the insect species against which a pest control composition containing a novel iminopyridine derivative represented by Formula (I) or at least one of acid addition salts thereof, and at least one of other pest control agents shows pest control effects include lepidopteran pests (for example, Spodoptera litura, cabbage armyworm, Mythimna separata, cabbageworm, cabbage moth, Spodoptera exigua, rice stem borer, grass leaf roller, tortricid, codling moth, leafminer moth, tussock moth, Agrotis spp), Helicoverpa spp, Heliothis spp and the like), hemipteran pests (for example, aphids (Aphididae, Adelgidae, Phylloxeridae) such as Myzus persicae, Aphis gossypii, Aphis fabae, corn leaf aphid, pea aphid, Aulacorthum solani, Aphis craccivora, Macrosiphum euphorbiae, Macrosiphum avenae, Methopolophium dirhodum, Rhopalosiphum padi, greenbug, Brevicoryne brassicae, Lipaphis erysimi, Aphis citricola, Rosy apple aphid, apple blight, Toxoptera aurantii and Toxoptera citricidus, leafhoppers such as Nephotettix cincticeps and Empoasca vitis, planthoppers such as Laodelphax striatellus, Nilaparvata lugens and Sogatella furcifera, Pentatomorpha such as Eysarcoris ventralis, Nezara viridula and Trigonotylus coelestialium, whiteflies (Aleyrodidae) such as silverleaf whitefly, Bemisia tabaci and greenhouse whitefly, and scale insects (Diaspididae, Margarodidae, Ortheziidae, Aclerdiae, Dactylopiidae, Kerridae, Pseudococcidae, Coccidae, Eriococcidae, Asterolecaniidae, Beesonidae, Lecanodiaspididae, Cerococcidae and the like) such as Pseudococcus comstocki, Planococcus citri, Pseudaulacaspis pentagona and Aonidiella aurantii), coleopteran pests (for example, Lissorhoptrus oryzophilus, Callosobruchus chinensis, Tenebrio molitor, Diabrotica virgifera virgifera, Diabrotica undecimpunctata howardi, Anomala cuprea, Anomala rufocuprea, Phyllotreta striolata, Aulacophora femoralis, Leptinotarsa decemlineata, Oulema oryzae, Bostrichidae, Cerambycidae and the like), Acarina (for example, Tetranychus urticae, Tetranychus kanzawai, Panonychus citri and the like), hymenopteran pests (for example, Tenthredinidae), orthopteran pests (for example, Acridioidea), dipteran pests (for example, Agromyzidae), thysanopteran pests (for example, Thrips palmi, Frankliniella occidentalis and the like), phytoparasitic nematode (for example, Meloidogyne, Pratylenchus, Aphelenchoides besseyi, Bursaphelenchus xylophilus and the like), and the like, examples of zooparasites include Ixodidae (for example, Amblyomma americanum, Amblyomma maculatum, Boophilus microplus, Dermacentor andersoni, Dermacentor occidentalis, Dermacentor variabilis, Haemaphysalis campanulata, Haemaphysalis flava, Haemaphysalis longicornis, Haemaphysalis megaspinosa Saito, Ixodes nipponensis, Ixodes ovatus, Ixodes pacifcus, Ixodes persulcatus, Ixodes ricinus, Ixodes scapularis, Ornithodoros moubata pacifcus and Rhipicephalus sanguineus), Cheyletidae (for example, Cheyletiella blakei and Cheyletiella yasguri), Demodex (for example, Demodex canis and Demodex cati), Psoroptidae (for example, Psoroptes communis), Sarcoptidae (for example, Chorioptes bovis and Otodectes cynotis), Dermanyssidae (for example, Ornithonyssus sylviarum), Dermanyssus gallinae, Pterolichus (for example, Megninia cubitalis and Pterolichus obtusus), Trombiculidae (for example, Helenicula miyagawai and Leptotrombidium akamushi), Shiphonaptera (for example, Ctenocephalides felis, Pulex irritans, Xenopsylla cheopis and Xenopsylla), Mallophaga (for example, Trichodectes canis and Menopon gallinae), Anoplura (for example, Haematopinus suis, Linognathus setosus, Pediculus humanus humanus, Pediculus humanus, Pthirus pubis and Cimex lectularius), Diptera (for example, Musca domestica, Hypoderma bovis, Stomoxys calcitrans and Gasterophilus), Psychodidae (for example, Phlebotomus), Glossina morsitans, Tabanidae, Ormosia tokionis (for example, Aedes albopictus and Aedes aegypti), Culicidae (for example, Culex pipiens pallens), Anophelini, Ceratopogonidae and the like), Simuliidae, Ceratopogonidae, Reduviidae, Monomorium pharaonic, Nematoda (for example, Strongyloides, Ancylostomatoidea, Strongyloidea (for example, Haemonchus contortus and Nippostrongylus braziliensis), Trichostrongyloidea, Metastrongyloidea (for example, Metastrongylus elongatus, Angiostrongylus cantonensis and Aelurostrongylus abstrutus), Oxyuroidea, Haterakoidea (for example, Ascaridia galli), Ascaridoidea (for example, Anisakis simplex, Ascaris suum, Parascaris equorum, Toxocara canis and Toxocara cati), Spiruroidea (for example, Subuluroidea, Gnathostoma spinigerum, Physaloptea praeputialis, Ascarops strongylina, Draschia megastoma and Ascaria hamulosa, Dracunculus medinensis), Filarioidea (for example, Dirofilaria immitis, lymphatic filarial, Onchocerca volvulus and Loa loa), Dioctophymatoidea, Trichinella (for example, Trichuris vulpis and Trichinella spiralis), Trematoda (for example, Schistosoma japonicum and Fasciola hepatica), Acanthocephala, Taenia (for example, Pseudophyllidea (for example, Spirometra erinaceieuropaei) and Cyclophyllidea (for example, Dipylidium caninum)), Protozoa, and the like, and examples of hygiene pests include Periplaneta (for example, Blattella germanica), Acaridae (for example, Tyrophagus putrescentiae), and Isoptera (for example, Coptotermes formosanus). Among them, preferred examples of an insect species, to which the pest control agent of the present invention is applied, include lepidopteran pests, hemipteran pests, thysanopteran pests, dipteran pests, coleopteran pests, zooparasitic Shiphonaptera or Acari, Dirofilaria immitis, Periplaneta and Isoptera (for example, at least one insect species selected from the group consisting of cabbage moth, Spodoptera litura, Aphis gossypii, Myzus persicae, Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Nephotettix cincticeps, Frankliniella occidentalis, Aulacophora femoralis, Oulema oryzae, Lissorhoptrus oryzophilus, Trigonotylus coelestialium, Musca domestica, Haemaphysalis longicornis, Dirofilaria immitis, Blattella germanica and Coptotermes formosanus), and particularly preferred examples thereof include cabbage moth, Aphis gossypii, Myzus persicae, Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Nephotettix cincticeps, Aulacophora femoralis, Oulema oryzae, Lissorhoptrus oryzophilus, Trigonotylus coelestialium, Musca domestica and Haemaphysalis longicornis.

In the present specification, examples of other pest control agents which may be mixed with the novel iminopyridine derivative represented by Formula (I) include an insecticide, a fungicide, a miticide, a herbicide, a plant growth regulator and a control agent for animal parasites, and examples of a specific chemical include those described in The Pesticide Manual (13th edition and published by the British Crop Protection Council) and the SHIBUYA INDEX (15th edition, 2010 and published by SHIBUYA INDEX RESEARCH GROUP).

Examples of other pest control agents which may be mixed with the novel iminopyridine derivative represented by Formula (I) preferably include an insecticide, a fungicide, a herbicide and a control agent for animal parasitic pests, and also those prepared by mixing a fungicide with an insecticide.

Preferred examples of other pest control agents which may be mixed with the novel iminopyridine derivative represented by Formula (I) include an organic phosphoric ester compound, a carbamate-based compound, a nereistoxin derivative, an organochlorine compound, a pyrethroid-based compound, a benzoyl urea-based compound, a juvenile hormone-like compound, a molting hormone-like compound, a neonicotinoid-based compound, a sodium channel blocker for nerve cells, an insecticidalmacrocyclic lactone, a γ-aminobutyric acid (GABA) antagonist, a ryanodine receptor agonistic compound, insecticidal ureas, a BT agent, an entomopathogenic viral agent and the like, as an insecticide, and more preferred examples thereof include an organic phosphoric ester compound such as acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, profenofos, pyraclofos, chlorpyrifos-methyl, diazinon, trichlorfon, tetrachlorvinphos, bromofenofos and cythioate, a carbamate-based compound such as methomyl, thiodicarb, aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb, pirimicarb, carbofuran and benfuracarb, a nereistoxin derivative such as cartap and thiocyclam, an organochlorine compound such as dicofol and tetradifon, a pyrethroid-based compound such as allethrin, d⋅d-T allethrin, dl⋅d-T80 allethrin, pyrethrins, phenothrin, flumethrin, cyfluthrin, d⋅d-T80 prarethrin, phthalthrin, transfluthrin, resmethrin, cyphenothrin, pyrethrum extract, synepirin222, synepirin500, permethrin, tefluthrin, cypermethrin, deltamethrin, cyhalothrin, fenvalerate, fluvalinate, ethofenprox and silafluofen, a benzoyl urea-based compound such as diflubenzuron, teflubenzuron, flufenoxuron, chlorfluazuron and lufenuron, a juvenile hormone-like compound such as methoprene and a molting hormone-like compound such as chromafenozide. In addition, examples of other compounds include buprofezin, hexythiazox, amitraz, chlordimeform, pyridaben, fenpyroxymate, Pyrimidifen, tebufenpyrad, tolfenpyrad, acequinocyl, cyflumetofen, flubendizmide, ethiprole, fipronil, etoxazole, imidacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram, thiacloprid, dinotefuran, pymetrozine, bifenazate, spirodiclofen, spiromesifen, spirotetramat, flonicamid, chlorfenapyr, pyriproxyfen, indoxacarb, pyridalyl, spinosad, spinetoram, avermectin, milbemycin, pyflubumide, cyenopyrafen, pyrifluquinazon, chlorantraniliprole, cyantraniliprole, lepimectin, metaflumizone, pyrafluprole, pyriprole, hydramethylnon, triazamate, sulfoxaflor, flupyradifurone, flometoquin, ivermectin, selamectin, moxidectin, doramectin, eprinomectin, milbemycin oxime, deet, metoxadiazon, cyromazine, triflumuron, star anise oil, triclabendazole, flubendazole, fenbendazole, antimony sodium gluconate, levamisole hydrochloride, bithionol, dichlorofen, phenothiazine, piperazine carbon bisulfide, piperazine phosphate, piperazine adipate, piperazine citrate, melarsomine dihydrochloride, metyridine, santonin, pyrantel pamoate, pyrantel, praziquantel, febantel, emodepside, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, an organic metal-based compound, a dinitro-based compound, an organic sulfur compound, a urea-based compound, a triazine-based compound, a hydrazine-based compound, and a compound represented by the following Formula (II) or agriculturally and zootechnically acceptable acid addition salts thereof. Examples of those acid addition salts include hydrochloride, nitrate, sulfate, phosphate, or acetate and the like.

[in the formula (II), Het1 represents a 3-pyridyl group,

R1 represents a hydroxyl group,

R2 and R3 represent a cyclopropylcarbonyloxy group, and

R4 represents a hydroxyl group]

More preferred examples of other insecticides which may be mixed with the novel iminopyridine derivative represented by Formula (I) include acetamiprid, imidacloprid, nitenpyram, clothianidin, acetamiprid, dinotefuran, thiacloprid, thiamethoxam, pymetrozine, spinosad, spinetram, fipronil, chloranthraniliprole, cyantraniliprole), cartap, thiocyclam, benfuracarb, buprofezin, ethofenprox, silafluofen, ethiprole, flonicamid, sulfoxaflor, flupyradifurone, flometoquin, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, afidopyropen, and the compound represented by Formula (II), or agriculturally and zootechnically acceptable acid addition salts thereof, and particularly preferred examples thereof include permethrin, acetamiprid, imidacloprid, clothianidin, dinotefuran, thiacloprid, thiamethoxam, pymetrozine, spinosad, spinetram, fipronil, chloranthraniliprole, cyantraniliprole, amitraz, ethofenprox, silafluofen, ethiprole, flonicamid, sulfoxaflor, flupyradifurone, flometoquin, ivermectin, moxidectin, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, and afidopyropen, or agriculturally and zootechnically acceptable acid addition salts thereof.

The novel iminopyridine derivative represented by Formula (I) may be used together or in combination with a microbial pesticide such as a BT agent and an entomopathogenic viral agent.

Examples of the fungicide which may be mixed with the novel iminopyridine derivative represented by Formula (I) include, for example, a strobilurin-based compound such as azoxystrobin, orysastrobin, kresoxym-methyl and trifloxystrobin, an anilinopyrimidine-based compound such as mepanipyrim, pyrimethanil and cyprodinil, an azole-based compound such as triadimefon, bitertanol, triflumizole, etaconazole, propic onazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, prochloraz and simec onazole, a quinoxaline-based compound such as quinomethionate, a dithiocarbamate-based compound such as maneb, zineb, mancozeb, polycarbamate and propineb, a phenyl carbamate-based compound such as diethofencarb, an organochlorine compound such as chlorothalonil and quintozene, a benzimidazole-based compound such as benomyl, thiophanate-methyl and carbendazole, a phenyl amide-based compound such as metalaxyl, oxadixyl, ofurase, benalaxyl, furalaxyl and cyprofuram, a sulfenic acid-based compound such as dichlofluanid, a copper-based compound such as copper hydroxide and copper oxyquinoline (oxine-copper), an isoxazole-based compound such as hydroxyisoxazole, an organic phosphorus-based compound such as fosetyl-aluminium and tolclofos-methyl, an N-halogenothioalkyl-based compound such as captan, captafol and folpet, a dicarboximide-based compound such as procymidone, iprodione and vinchlozolin, a benzanilide-based compound such as thifluzamide, furametpyr, flutolanil and mepronil, a morpholine-based compound such as fenpropimorph and dimethomorph, an organic tin-based compound such as fenthin hydroxide and fenthin acetate, a cyanopyrrole-based compound such as fludioxonil and fenpiclonil, 9-membered cyclic dilactone compounds such as acibenzolar-S-methyl, isotianil, tiadinil, carpropamid, diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, fthalide, fluazinam, cymoxanil, triforine, pyrifenox, probenazole, fenarimol, fenpropidin, pencycuron, cyazofamid, iprovalicarb, tebufloquin, benthiavalicarb-isopropyl, tolprocarb, validamycin, Kasugamycin, Streptomycin and UK-2As, a compound represented by the following Formula (III), which is described in JP-A No. 2009-078991, a compound represented by the following Formula (IV), which is described in Republication No. WO08/066148, and a compound represented by the following Formula (V), which is described in Republication No. WO09/028280, or agriculturally and zootechnically acceptable acid addition salts thereof.

[in the formula (III), R1 and R2 represent a hydrogen atom or a haloalkyl group having 1 to 6 carbon atoms and the like (however, at least one of R1 and R2 represents a haloalkyl group having 1 to 6 carbon atoms), R3 represents a hydrogen atom and the like, A represents OR4, SR5, NR6R7 or NR8NR9R10, R4 represents an alkyl group having 8 to 12 carbon atoms and the like, R5 represents an alkyl group having 1 to 12 carbon atoms and the like, R6 and R7 represent a hydrogen atom or an alkyl group having 8 to 12 carbon atoms, and R8, R9 and R10 represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms and the like]

[in the formula (IV), R1 and R2 represent a C1 to C6 alkyl group, an aryl group, a heteroaryl group, or a aralkyl group,

R3 and R4 represent a hydrogen atom, a C1 to C6 alkyl group, a halogen atom, or a C1 to C6 alkoxy group,

X represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, a C2 to C6 alkenyl group, a C2 to C6 alkynyl group, an aryl group, a heteroaryl group, or a C1 to C6 alkoxy group,

Y represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, or a C1 to C 6 alkoxy group, and

n represents 0 to 4, and m represents 0 to 6]

[in the formula (V), R1 represents an alkyl group and the like, R2 and R3 each independently represent a hydrogen atom, a haloalkyl group and the like (however, at least one of R2 and R3 is a haloalkyl group having 1 to 6 carbon atoms), A represents —OR4, —SR5, —NR6R7 or —NR8NR9R10, R4 represents an alkyl group having 3 to 12 carbon atoms, R5 represents an alkyl group having 1 to 12 carbon atoms, R6 represents a hydrogen atom, R7 represents an alkyl group having 5 to 12 carbon atoms, and R8, R9 and R10 each represent an alkyl group having 3 to 12 carbon atoms and the like, an alkyl group having 1 to 12 carbon atoms and the like, a hydrogen atom and the like, an alkyl group having 5 to 12 carbon atoms and the like, and an alkyl group having 1 to 12 carbon atoms, respectively.]

More preferred examples of other fungicides which may be mixed with the novel iminopyridine derivative represented by Formula (I) include azoxystrobin, orysastrobin, thifluzamide, furametpyr, fthalide, probenazole, acibenzolar-S-methyl, tiadinil, isotianil, carpropamid, diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, tebufloquin, simeconazole, validamycin, kasugamycin and pencycuron, and particularly preferred examples thereof include probenazole and tebufloquin.

Preferred examples of other pest control agents which may be mixed with the novel iminopyridine derivatives represented by Formula (I) also include herbicides such as lipid synthesis inhibitors, acetolactate synthesis inhibitors, photosystem inhibitors, protoporphyrinogen IX oxidation inhibitors, bleacher herbicides, amino acid synthesis inhibitors, dihydropteroate synthetase inhibitors, cell division inhibitors, very-long-chain fatty acid synthesis inhibitors, cellulose biosynthesis inhibitors, decoupling agents, auxin-like herbicides, auxin transport inhibitors, and the like. Specific examples here are alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-P-methyl, haloxyfop-P, haloxyfop-P-methyl ester, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate, ethyl dipropylthiocarbamat (EPIC), esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, trichloroacetic acid (TCA), thiobencarb, tiocarbazil, triallate, vernolate, sulfonylureas (amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl, and tritosulfuron), imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, triazolopyrimidine herbicides (chloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan, and pyroxsulam), bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, flucarbazone, flucarbazone-sodium, propoxycarbazon, propoxycarbazon-sodium, thiencarbazone, thiencarbazone-methyl, triazine herbicides (chlorotriazine, triazinones, triazindiones, methylthiotriazines, and pyridazinones (for example, ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin, prometon, prometryn, propazine, simazin, simetryn, terbumeton, terbuthylazin, terbutryn, and trietazin)), arylureas (for example, chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, and thiadiazuron), phenylcarbamate esters (for example, desmedipham, karbutilat, phenmedipham, and phenmedipham-ethyl), nitrile herbicides (for example, bromofenoxim, bromoxynil and its salts and esters, and ioxynil and its salts and esters), uracils (for example, bromacil, lenacil, and terbacil), bentazon, bentazon-sodium, pyridate, pyridafol, pentanochlor, propanil, inhibitors of the photosystem (such as diquat, diquat-dibromide, paraquat, paraquatdichloride, and paraquat dimethyl sulfate), acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, ozadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, pyrazolate, picolinafen, aclonifen, amitrole, clomazone, flumeturon, glyphosate and its salts, bialaphos, bialaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium, asulam, dinitroanilines (for example, benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, and trifluralin), phosphoramidate herbicides (for example, amiprophos, amiprophos-methyl, and butamifos), benzoic acid herbicides (for example, chlorthal and chlorthal-dimethyl), pyridines (for example, dithiopyr and thiazopyr), benzamides (for example, propyzamide and tebutam), chloroacetamides (for example, acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamide, pretilachlor, propachlor, propisochlor, and thenylchlor), oxyacetanilides (for example, flufenacet and mefenacet), acetanilides (for example, diphenamide, naproanilide, and napropamide), tetrazolinones (for example, fentrazamide), anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, chlorthiamid, dichlobenil, flupoxam, isoxaben, dinoseb, dinoterb, 4,6-dinitro-o-cresol (DNOC) and its salts, 2,4-D and its salts and esters, 2,4-B and its salts and esters, aminopyralid and its salts (for example, aminopyralid-tris(2-hydroxypropyl)ammonium) and esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr and its salts and esters, 2-methyl-4-chlorophenoxyacetic acid (MCPA) and its salts and esters, MCPA-thioethyl, 4-(2-methyl-4-chlorophenoxy)butyric acid (MCPB) and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, 2,3,6-trichlorobenzoic acid (TBA (2,3,6)) and its salts and esters, triclopyr and its salts and esters, aminocyclopyrachlor and its salts and esters, diflufenzopyr and its salts, naptalam and its salts, bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-methyl sulfate, dimethipin, disodium methanearsonate (DSMA), dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane, and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters.

Control agents for animal parasitic pests which may be mixed with the novel iminopyridine derivatives represented by Formula (I) can be exemplified by organophosphate ester compounds, carbamate-based compounds, nereistoxin derivatives, organochlorine compounds, pyrethroid-based compounds, benzoyl urea-based compounds, juvenile hormone-like compounds, molting hormone-like compounds, neonicotinoid-based compounds, sodium channel blockers for nerve cells, insecticidal macrocyclic lactones, γ-aminobutyric acid (GABA) antagonists, ryanodine receptor agonistic compounds, insecticidal ureas, and the like. More preferred specific examples include organophosphate esters such as dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, profenofos, pyraclofos, chlorpyrifos-methyl, diazinon, trichlorfon, tetrachlorvinphos, bromofenofos, cythioate, and fenthion; carbamate-based compounds such as methomyl, thiodicarb, aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb, pirimicarb, carbofuran, and benfuracarb; nereistoxin derivatives such as cartap and thiocyclam; organochlorine compounds such as dicofol and tetradifon; pyrethroid-based compounds such as allethrin, d⋅d-T allethrin, dl⋅d-T80 allethrin, pyrethrins, phenothrin, flumethrin, cyfluthrin, d⋅d-T80 prarethrin, phthalthrin, transfluthrin, resmethrin, cyphenothrin, pyrethrum extract, synepirin 222, synepirin 500, permethrin, tefluthrin, cypermethrin, deltamethrin, cyhalothrin, fenvalerate, fluvalinate, ethofenprox, and silafluofen; benzoyl urea-based compounds such as diflubenzuron, teflubenzuron, flufenoxuron, chlorfluazuron, and lufenuron; juvenile hormone-like compounds such as methoprene; molting hormone-like compounds such as chromafenozide; and other compounds such as amitraz, chlordimeform, fipronil, etoxazole, imidacloprid, clothianidin, thiamethoxam, acetamiprid, nitenpyram, thiacloprid, dinotefuran, spirodiclofen, pyriproxyfen, indoxacarb, spinosad, spinetoram, avermectin, milbemycin, metaflumizone, pyrafluprole, pyriprole, hydramethylnon, triazamate, sulfoxaflor, flupyradifurone, ivermectin, selamectin, moxidectin, doramectin, eprinomectin, milbemycin oxim, diethylcarbamazine citrate, deet, metoxadiazon, cyromazine, triflumuron, star anise oil, triclabendazole, flubendazole, fenbendazole, antimony sodium gluconate, levamisole hydrochloride, bithionol, dichlorofen, phenothiazine, piperazine carbon bisulfide, piperazine phosphate, piperazine adipate, piperazine citrate, melarsomine dihydrochloride, metyridine, santonin, pyrantel pamoate, pyrantel, praziquantel, febantel, emodepside, derquantel, monopantel, emamectin benzoate, cycloxaprid, and a compound represented by the following Formula (VI) or agriculturally and zootechnically acceptable acid addition salts thereof. Examples of those acid addition salts include hydrochloride, nitrate, sulfate, phosphate, or acetate and the like.

More preferred examples are flumethrin, permethrin, fipronyl, pyriprol, imidacloprid, thiamethoxam, acetamiprid, dinotefuran, amitraz, metaflumizon, pyriproxyfen, fenitrothion, lufenuron, ethoxazol, spinosad, spinetoram, emodepside, emamectin benzoate, ivermectin, selamectin, moxidectin, doramectin, eprinomectin, derquantel, and monopantel.

Particularly preferred examples include amitraz and the like.

When the pest control composition is a pest control agent for agricultural and horticultural, particularly preferred examples for the present invention are pest control compositions in which the novel iminopyridine derivative represented by Formula (I) is at least one compound selected from N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P212), N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (compound 1-20), or N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-isopropylacetimidamide (compound 1-45), and the other pest control agent includes at least one insecticide or fungicide selected from acetamiprid, imidacloprid, clothianidin, dinotefuran, thiacloprid, fipronil, thiamethoxam, pymetrozine, flonicamid, spinosad, cyantraniliprole, chloranthraniliprole, ethofenprox, silafluofen, ethiprole, sulfoxaflor, flupyradifurone, flometoquin, emamectin benzoate, cycloxaprid, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, and afidopyropen, orysastrobin, thifluzamide, furametpyr, fthalide, probenazole, acibenzolar-S-methyl, tiadinil, isotianil, carpropamid, diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, tebufloquin, azoxystrobin, simeconazole, validamycin, thifluzamide, furametpyr, and pencycuron.

The pest control composition of the present invention may be prepared using the novel iminopyridine derivative represented by Formula (I), other insecticides, fungicides, herbicides, or control agents for animal parasites, and an agriculturally and zootechnically acceptable carrier (solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant, and other preparation adjuvants).

(Specific Examples of Pesticide Preparations)

When the pest control composition of the present invention is a pest control agent for agricultural and horticultural, the composition is usually mixed with an agriculturally and horticulturally acceptable carrier (solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant and other adjuvants for preparation to be provided in any formulation form of emulsifiable concentrates, liquid formulations, suspensions, wettable powders, flowables, dust, granules, tablets, oils, aerosols, fumigants and the like.

Examples of the solid carrier include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate and the like.

Examples of the liquid carrier include alcohols such as methanol, n-hexanol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aliphatic hydrocarbons such as n-hexane, kerosene and lamp oil, aromatic hydrocarbons such as toluene, xylene and methyl naphthalene, ethers such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyl nitrile, acid amides such as dimethylformamide and dimethylacetamide, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, water and the like.

Further, examples of the gaseous carrier include LPG, air, nitrogen, carbonic acid gas, dimethyl ether and the like.

As the surfactant or dispersant for emulsification, dispersion, spreading and the like, it is possible to use, for example, alkylsulfate esters, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydricalcohol esters, lignin sulfonates or the like.

In addition, as the adjuvant for improving the properties of the preparation, it is possible to use, for example, carboxymethylcellulose, gum arabic, polyethylene glycol, calcium stearate or the like.

The aforementioned solid carriers, liquid carriers, gaseous carriers, surfactants, dispersants and adjuvants may be used either alone or in combination, if necessary.

The content of active ingredients in the preparation is not particularly limited, but is usually in the range of 1 to 75% by weight for the emulsifiable concentrate, 0.3 to 25% by weight for the dust, 1 to 90% by weight for the wettable powder, and 0.5 to 10% by weight for the granular formulation.

The novel iminopyridine derivatives represented by Formula (I), a preparation including the same and a mixed formulation of other pest control agents with the same may be applied to pest insects, plants, plant propagation materials (for example, seeds, plant leaves and stems, roots, soil, water surface and materials for cultivation), rooms which require disturbing the invasion of pests and the like. The application thereof may be performed before and after the invasion of pests.

A pest control agent including at least one of the novel iminopyridine derivatives represented by Formula (I) may also be applied to genetically-modified crops.

In a preferred aspect thereof, examples of a pest control composition further including an agriculturally and horticulturally acceptable carrier include:

(1) a wettable powder composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 0.6 to 30% by weight of a wetting agent and a dispersant, and 20 to 95% by weight of an extender,

(2) a water dispersible granule composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 0.6 to 30% by weight of a wetting agent, a dispersant and a binder, and 20 to 95% by weight of an extender,

(3) a flowable composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 5 to 40% by weight of a dispersant, a thickener, an antifreeze, an antiseptic and an antifoaming agent, and 20 to 94% by weight of water,

(4) an emulsifiable concentrate composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 1 to 30% by weight of an emulsifier and an emulsion stabilizer, and 20 to 97% by weight of an organic solvent,

(5) a dust composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, and 70 to 99.8% by weight of an extender,

(6) a low drift dust composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, and 70 to 99.8% by weight of an extender,

(7) a microgranule fine composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 0.2 to 10% by weight of a solvent or binder, and 70 to 99.6% by weight of an extender,

(8) a granule composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 0.5 to 30% by weight of a granulation auxiliary (surfactant) and a binder, and 20 to 98% by weight of an extender, and

(9) a microcapsule composition containing 0.1 to 80% by weight of the novel iminopyridine derivative represented by Formula (I), 0.1 to 80% by weight of an insecticide as another pest control agent, 1 to 50% by weight of a covering agent, an emulsifier, a dispersant and an antiseptic, and 20 to 98% by weight of water. Preferably, examples thereof include compositions of (2), (3), (6) and (8)

(Specific Examples of Formulations for Animals)

When the pest control agent of the present invention is a control agent for animal parasitic pests, the agent is provided in the form of liquid formulations, emulsifiable concentrates, liquid drops, sprays, foam preparations, granules, fine granules, dust, capsules, pills, tablets, chewable formulations, injections, suppositories, creams, shampoos, rinses, resin agents, fumigants, poison baits and the like, and is particularly preferably provided in the form of liquid formulations and liquid drops. These forms can be prepared using the following pharmaceutically acceptable carriers.

The liquid formulation may also be blended with a typical adjuvant for preparation, such as an emulsifier, a dispersant, a spreading agent, a wetting agent, a suspending agent, a preservative and a propellant, and may also be blended with a typical film former. As the surfactant for emulsification, dispersion, spreading and the like, it is possible to use, for example, soaps, polyoxyalkylene alkyl (aryl) ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene fatty acid ester, higher alcohols, alkyl aryl sulfonates and the like. Examples of dispersants include casein, gelatin, polysaccharides, lignin derivatives, saccharides, synthetic water soluble polymers and the like. Examples of spreading⋅wetting agents include glycerin, polyethylene glycol and the like. Examples of suspending agents include casein, gelatin, hydroxypropylcellulose, gum arabic and the like, and examples of stabilizers include phenolic antioxidants (BHT, BHA and the like), amine antioxidants (diphenylamine and the like), organic sulfur antioxidants and the like. Examples of preservatives include methyl p-oxybenzoate, ethyl p-oxybenzoate, propyl p-oxybenzoate, butyl p-oxybenzoate and the like. The aforementioned carriers, surfactants, dispersants and adjuvants may be used either alone or in combination, if necessary. Furthermore, perfumes, synergists and the like may also be incorporated. The suitable content of the active ingredients in the pest control agent of the present invention is usually 1 to 75% by weight for the liquid formulation.

Examples of carriers used for the preparation of creams include non-volatile hydrocarbons (liquid paraffin and the like), lanolin hydrogenated fats and oils, higher fatty acids, fatty acid esters, animal and vegetable oils, silicone oils, water and the like. Further, emulsifiers, humectants, antioxidants, perfumes, borax and ultraviolet absorbers may also be used either alone or in combination, if necessary. Examples of emulsifiers include fatty acid sorbitan, polyoxyethylene alkyl ethers, and fatty acid polyoxyethylene and the like. The suitable content of the active ingredients in the pest control agent of the present invention is usually 0.5 to 75% by weight for the cream.

The capsules, pills or tablets may be used such that the active ingredients in the composition of the present invention are mixed with a carrier such as starch, lactose or talc, a disintegrator and/or a binder, such as magnesium stearate is added thereto, and, if necessary, the mixture is tableted.

Carriers for the preparation of injections need to be prepared as an aseptic solution, but the solution may contain other substances, for example, a salt or glucose enough to isotonicate the solution with blood. As available carriers, “injections need to be prepared as an aseptic solution. For injections, the solution may contain, for example, a salt or glucose enough to isotonicate the solution with blood. Examples of available carriers for the preparation of injections include esters such as fatty acid derivatives of glyceride, benzyl benzoate, isopropyl myristate and propylene glycol, and organic solvents such as N-methylpyrrolidone and glycerol formal. The content of the active ingredients in the pest control agent of the present invention is usually 0.01 to 10% by weight for the injection.

Examples of carriers for the preparation of resin agents include vinyl chloride polymers, polyurethane and the like. Plasticizers such as phthalic acid esters, adipic acid esters and stearic acid may be added to these bases, if necessary. After the active ingredients are kneaded into the base, the kneaded product may be molded by injection molding, extrusion molding, press molding and the like. In addition, the molded product may also be properly subjected to processes such as molding or cutting to form an ear tag for animals or insecticidal collar for animals.

Examples of carriers for toxic baits include bait substances and attraction substances (farina such as wheat flour and corn flour, starch such as corn starch and potato starch, saccharides such as granulated sugar, malt sugar and honey, food flavors such as glycerin, onion flavor and milk flavor, animal powders such as pupal powder and fish powder, various pheromones and the like). The suitable content of the active ingredients in the pest control agent of the present invention is usually 0.0001 to 90% by weight for the toxic bait.

The pest control composition according to the present invention may be used such that a preparation form prepared by independently including at least one of the novel iminopyridine derivative represented by Formula (I) as the active ingredient in the composition, or acid addition salts thereof and at least one of other pest control agents alone is formulated and these ingredients when used are mixed on the spot.

Therefore, according to another aspect of the present invention, there is provided a combined product prepared by including at least one of the novel iminopyridine derivative represented by Formula (I) as the active ingredient or acid addition salts thereof and at least one of other pest control agents.

According to another preferred aspect of the present invention, in the combined product, the novel iminopyridine derivative represented by Formula (I) or acid addition salts thereof is provided as a first composition prepared by including the same as active ingredients, and other pest control agents is provided as a second composition prepared by including the same as active ingredients. In this case, the first composition and the second composition may be any formulation form which uses appropriate carriers or adjuvants in combination thereof in the same manner as in the case of the aforementioned pest control composition. The combined product may be provided in the form of a pharmaceutical set.

According to still another aspect of the present invention, there is provided a method for protecting useful plants or animals from pests, including: simultaneously or independently (preferably, each ingredient simultaneously) applying at least one of the novel iminopyridine derivative represented by Formula (I), enantiomers thereof, mixtures thereof or acid addition salts thereof as an active ingredient and at least one of other pest control agents to a region to be treated.

In the method, “simultaneously” applying also includes mixing at least one of the novel iminopyridine derivative represented by Formula (I) or acid addition salts thereof and at least one of other pest control agents before being applied to a region to be treated, and applying the mixture thereto. “Independently” applying includes, without mixing these ingredients in advance, applying the novel iminopyridine derivative represented by Formula (I) or acid addition salts thereof earlier than the other ingredients, or applying the novel iminopyridine derivative represented by Formula (I) or acid addition salts thereof later than the other ingredients.

According to still another preferred aspect of the present invention,

there is provided a method for protecting useful plants or animals from pests, including: applying

(1) a first composition prepared by including at least one of the novel iminopyridine derivative represented by Formula (I) or acid addition salts thereof as an active ingredient, and

(2) a second composition prepared by including at least one of other pest control agents as an active ingredient

to a region to be treated.

According to yet another aspect of the present invention, there is provided a method for protecting useful plants from pests, including: applying the composition or combined product of the present invention as it is or diluted to pests, useful plants, seeds of useful plants, soil, cultivation carriers or animals as a target, and preferably to useful plants, soil or animals.

According to still yet another aspect of the present invention, there is provided a use of the composition or combined product of the present invention in order to protect useful plants or animals from pests.

Furthermore, preferred examples of the method for applying the composition or combined product of the present invention to pests, useful plants, seeds of useful plants, soil or cultivation carriers as a target include spray treatment, water surface treatment, soil treatment (mixing, irrigation and the like), nursery box treatment, surface treatment (application, dust coating and covering) or fumigation treatment (treatment in enclosed space, such as covering soil with a polyfilm after soil injection) and the like, and more preferred examples include water surface treatment, soil treatment, nursery box treatment or surface treatment.

The throughput in the case of application to plants by spray treatment is 0.1 g to 10 kg per 10 areas of cultivated land and preferably 1 g to 1 kg, as an amount of active ingredients of the composition of the present invention.

Further, examples of a method for treating seeds, roots, tubers, bulbs or rhizomes of plants include a dipping method, a dust coating method, a smearing method, a spraying method, a pelleting method, a coating method and a fumigating method for the seed. The dipping method is a method in which seeds are dipped in a liquid chemical solution, and the dust coating method is classified into a dry dust coating method in which a granular chemical is adhered onto dry seeds, and a wet dust coating method in which a powdery chemical is adhered onto seeds which have been slightly soaked in water. In addition, the smearing method is a method in which a suspended chemical is applied on the surface of seeds within a mixer and the spraying method is a method in which a suspended chemical is sprayed onto the surface of seeds. Furthermore, the pelleting method is a method in which a chemical is mixed with a filler and treated when seeds are pelleted together with the filler to form pellets having certain size and shape, the coating method is a method in which a chemical-containing film is coated onto seeds, and the fumigating method is a method in which seeds are sterilized with a chemical which has been gasified within a hermetically sealed container.

Examples of the preferred treatment method of the composition of the present invention include a dipping method, a dust coating method, a smearing method, a spraying method, a pelleting method and a coating method.

Further, the composition of the present invention may also be used to, in addition to seeds, germinated plants which are transplanted after germination or after budding from soil, and embryo plants. These plants may be protected by the treatment of the whole or a part thereof by dipping before transplantation.

The throughput in the case of application to seeds of plants is not particularly limited, but preferably 1 g to 10 kg and more preferably 100 g to 1 kg per 100 kg of seeds, as an amount of active ingredients of the composition of the present invention.

In addition, the method for application of the composition of the present invention to soil is not particularly limited, but preferred application methods are as follows.

Examples of the method include a method in which granules including the composition of the present invention are applied into soil or on soil. Particularly preferred soil application methods include spraying, stripe application, groove application, and planting hole application.

Furthermore, application by irrigating soil with a solution prepared by emulsifying or dissolving the composition of the present invention in water is also a preferred soil application method.

Besides these methods, examples of preferred soil application methods include application into a nutrient solution in nutrient solution culture systems such as solid medium culture, for example, hydroponic culture, sand culture, NFT (nutrient film technique), rock wool culture and the like for the production of vegetables and flowering plants, or application into a nursery box for paddy rice seedling (mixing with bed soil and the like). The compound of the present invention may be applied directly to artificial culture soil including vermiculite and a solid medium including an artificial mat for growing seedling.

The throughput of the composition of the present invention into water surface, a nursery box or soil is not particularly limited, but is 0.1 g to 10 kg of preferably active ingredients per 10 ares of cultivated land and preferably 1 g to 1 kg. Further, as the method for applying the composition or combined product of the present invention to an applied organism, it is possible to control pests by administering the pest control composition of the present invention into the applied organism either orally or by injection, wholly or partly administering the composition into the body surface of an applied animal, or mounting the pest control agent formulated into a resin preparation or sheet preparation on the applied organism. In addition, it is also possible to control pests by covering places in which the invasion, parasitism and movement of pests are expected with the pest control composition of the present invention.

The pest control composition of the present invention may be used as it is, but may be diluted with water, liquid carriers, commercially available shampoos, rinses, baits, breed cage bottoms and the like and applied in some cases. When the pest control composition of the present invention is diluted with a dilution liquid (water) such as an emulsifiable concentrate, a flowable and a wettable powder and used, the amount is not particularly limited, but, preferably, the composition is applied by diluting the composition in water and spraying the mixture such that the concentration of active ingredients is 10 to 10,000 ppm. Furthermore, when the pest control composition of the present invention is administered to a target organism, the administration amount thereof is not particularly limited, but when the composition is percutaneously applied, the amount of the composition is preferably in a range from 0.01 to 500 mg per 1 kg of the body weight of the target organism. When the composition is orally administered, the amount of the composition is in a range from 0.01 to 100 mg per 1 kg of the body weight of the target organism. When a resin preparation is mounted on the target organism, the amount of the composition contained in the resin preparation is preferably in a range from 0.01 to 50% by weight per weight of the resin preparation.

EXAMPLES

Hereinafter, the present invention will be specifically described with reference to Examples, but the present invention is not limited to the Examples.

Synthetic Example P1: N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P212)

(1) 25 g (270 mmol) of 2-aminopyridine was dissolved in 200 ml of anhydrous dichloromethane, 41 ml (30 g, 300 mmol) of triethylamine was added thereto, and the mixture was cooled to 0° C. 38 ml (57 g, 270 mmol) of anhydrous trifluoroacetic acid was added dropwise thereto over 15 minutes, and the resulting mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was injected into about 100 ml of iced water, and the mixture was stirred for 10 minutes. The mixture was transferred to a separatory funnel to perform liquid separation, and the organic layer was washed twice with 150 ml of water and twice with 150 ml of a 1% HCl aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 36 g (yield 71%) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene) acetamide.

1H-NMR (CDCl3, δ, ppm): 7.20 (1H, ddd), 7.83 (1H, td), 8.20 (1H, d), 8.35 (1H, d), 10.07 (1H, brs) 13C-NMR (CDCl3, δ, ppm): 115.3, 115.5 (q), 121.6, 139.1, 147.9, 149.5, 155.3 (q)

MS: m/z=191 (M+H)

(2) 20 g (126 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 200 ml of anhydrous acetonitrile, 24 g (126 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by the above-described method and 21 g (151 mmol) of potassium carbonate were added thereto, and the resulting mixture was heated and refluxed for 6 hours, and then stirred at room temperature for 10 hours. After the reaction was completed, the reaction solution was filtered and the liquid was concentrated under reduced pressure. Diethyl ether was added thereto for crystallization, and the crystals thus obtained were collected and washed well with diethyl ether and water. The crystals thus obtained were dried under reduced pressure at 60° C. for 1 hour to obtain the subject material. Amount obtained 26 g (yield 66%).

1H-NMR (CDCl3, δ, ppm): 5.57 (2H, s), 6.92 (1H, td), 7.31 (1H, d), 7.80 (1H, td), 7.87 (1H, dd), 7.99 (1H, dd), 8.48 (2H, m)

13C-NMR (CDCl3, δ, ppm): 53.8, 115.5, 117.2 (q), 122.1, 124.7, 130.0, 139.2, 140.0, 142.5, 149.7, 151.8, 158.9, 163.5 (q)

MS: m/z=316 (M+H)

(3) Powder X-Ray Crystal Analysis

In the powder X-ray diffraction, measurement was performed under the following conditions.

Device name: RINT-2200 (Rigaku Corporation)

X-ray: Cu-Kα (40 kV, 20 mA)

Scanning range: 4 to 40°, sampling width: 0.02° and scanning rate: 1°/min

The results are as follows.

Diffraction angle (20) 8.7°, 14.2°, 17.5°, 18.3°, 19.8°, 22.4°, 30.9° and 35.3°

(4) Differential Scanning Calorimetry (DSC)

In the differential scanning calorimetry, measurement was performed under the following conditions.

Device name: DSC-60

Sample cell: aluminum

Temperature range: 50° C. to 250° C. (heating rate: 10° C./min)

As a result, the melting point was observed at 155° C. to 158° C.

Another method of Synthetic Example P1

3.00 g (18.6 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 20 ml of anhydrous DMF, 1.75 g (18.6 mmol) of 2-aminopyridine was added thereto, and the resulting mixture was stirred at 80° C. for 8 hours and at room temperature for 5 hours. After the reaction was completed, DMF was distilled off under reduced pressure, acetonitrile was added thereto to precipitate a solid, and the solid was collected, washed well with acetonitrile and dried to obtain 2.07 g (yield 44%) of 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride.

1H-NMR (DMSO-d6, δ, ppm): 5.65 (2H, s), 6.96 (1H, t), 7.23 (1H, m), 7.57 (1H, d), 7.80 (1H, m), 7.91 (1H, m), 8.28 (1H, m), 8.49 (1H, d), 9.13 (2H, brs)

50 mg (0.20 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the above-described method was dissolved in 5 ml of anhydrous dichloromethane, 122 mg (1.00 mmol) of DMAP and 50 mg (0.24 mmol) of anhydrous trifluoroacetic acid were added thereto in sequence under ice cold conditions, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed with 1% hydrochloric acid, and then dried over anhydrous magnesium sulfate. Dichloromethane was distilled off under reduced pressure to obtain the subject material. Amount obtained 42 mg (yield 67%). NMR was the same as that of the above-described method.

Synthetic Example P2: 2,2-dibromo-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-acetamide (Compound P241)

200 mg (0.78 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the method described in another method of Synthetic Example P1, 238 mg (1.95 mmol) of DMAP and 224 mg (1.17 mmol) of EDC-HCl were dissolved in 10 ml of anhydrous dichloromethane, 101 μl (202 mg, 1.17 mmol) of dibromoacetic acid was added thereto, and the resulting mixture was stirred at room temperature overnight. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twice with a 1% HCl aqueous solution, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the subject material. Amount obtained 50 mg (yield 15%)

1H-NMR (CDCl3, δ, ppm): 5.56 (2H, s), 5.99 (1H, s), 6.78 (1H, td), 7.33 (1H, d), 7.69 (1H, td), 7.76 (1H, dd), 7.93 (1H, dd), 8.39 (1H, d), 8.50 (1H, d)

13C-NMR (CDCl3, δ, ppm): 44.6, 53.1, 113.7, 121.9, 124.8, 130.1, 138.2, 139.7, 141.2, 149.5, 152.0, 159.4, 172.2

MS: m/z=418 (M+H)

Synthetic Example P3: N-[1-((6-chloro-5-fluoropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P227)

4.00 g (27.6 mmol) of 2-chloro-3-fluoro-5-methyl pyridine was dissolved in 80 ml of carbon tetrachloride, 7.37 g (41.4 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed overnight. After the reaction was completed, the reaction solution was returned to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to obtain 3.06 g (yield 51%) of 5-(bromomethyl)-2-chloro-3-fluoropyridine.

1H-NMR (CDCl3, δ, ppm): 4.45 (2H, s), 7.54 (1H, dd), 8.23 (1H, s)

50 mg (0.22 mmol) of the 5-(bromomethyl)-2-chloro-3-fluoropyridine obtained by the aforementioned method was dissolved in 5 ml of anhydrous acetonitrile, 42 mg (0.22 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide obtained by the method described in (1) of Reference Example 1 and 36 mg (0.26 mmol) of potassium carbonate were added thereto in sequence, and the resulting mixture was heated and refluxed for 7 hours. After the reaction was completed, the reaction solution was returned to room temperature to filter insoluble materials, and the filtrate was concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected, washed with diethyl ether, and then dried under reduced pressure in a desiccator to obtain the subject material. Amount obtained 29 mg (yield 40%).

1H-NMR (CDCl3, δ, ppm): 5.54 (2H, s), 6.89 (1H, td), 7.76 (1H, dd), 7.80 (1H, td), 7.85 (1H, d), 8.29 (1H, d), 8.57 (1H, d)

MS: m/z=334 (M+H)

Synthetic Example P4: N-[1-((6-fluoropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P229)

500 mg (4.50 mmol) of 2-fluoro-5-methyl pyridine was dissolved in 50 ml of carbon tetrachloride, 1.20 g (6.76 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 2.5 hours. After the reaction was completed, the reaction solution was returned to room temperature, and the solvent was distilled off under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to obtain 300 mg (yield 35%) of 5-bromomethyl-2-fluoropyridine.

57 mg (0.30 mmol) of the 5-bromomethyl-2-fluoropyridine obtained by the aforementioned method was dissolved in 10 ml of anhydrous acetonitrile, 57 mg (0.30 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide synthesized by the method described in (1) of Synthetic Example P1 and 69 mg (0.50 mmol) of potassium carbonate were added thereto in sequence, and the resulting mixture was heated and refluxed for 6 hours. After the reaction was completed, the reaction solution was returned to room temperature to filter insoluble materials, and the filtrate was concentrated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→3:1) to obtain the subject material. Amount obtained 21 mg (yield 23%).

1H-NMR (CDCl3, δ, ppm): 5.56 (2H, s), 6.89 (1H, td), 6.94 (1H, d), 7.79 (1H, td), 7.87 (1H, d), 8.03 (1H, m), 8.31 (1H, s), 8.54 (1H, d)

MS: m/z=300 (M+H)

Synthetic Example P5: N-[1-((6-bromopyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P231)

500 mg (2.92 mmol) of 2-bromo-5-methylpyridine was dissolved in 15 ml of carbon tetrachloride, 623 mg (3.50 mmol) of N-bromosuccinimide and 10 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 19 hours. After the reaction was completed, the reaction solution was returned to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to obtain 143 mg (yield 20%) of 2-bromo-5-bromomethylpyridine.

1H-NMR (CDCl3, δ, ppm): 4.42 (2H, s), 7.47 (1H, d), 7.59 (1H, dd), 8.38 (1H, d)

70 mg (0.28 mmol) of the 2-bromo-5-bromomethylpyridine obtained by the aforementioned method was dissolved in 10 ml of anhydrous acetonitrile, 54 mg (0.28 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide synthesized by the method described in (1) of Synthetic Example P1 and 46 mg (0.34 mmol) of potassium carbonate were added thereto in sequence, and the resulting mixture was heated and refluxed for 6 hours. After the reaction was completed, the reaction solution was returned to room temperature to filter insoluble materials, and the filtrate was concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected, washed with diethyl ether, and then dried under reduced pressure in a desiccator to obtain the subject material. Amount obtained 81 mg (yield 82%).

1H-NMR (CDCl3, δ, ppm): 5.52 (2H, s), 6.88 (1H, t), 7.48 (1H, d), 7.78 (2H, m), 7.84 (1H, d), 8.44 (1H, d), 8.53 (1H, d)

MS: m/z=360 (M+H)

Synthetic Example P6: 2-chloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-acetamide (Compound P236)

70 mg (0.27 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the method described in another method of Synthetic Example P1 was dissolved in 4 ml of anhydrous dichloromethane, 82 mg (0.67 mmol) of DMAP, 25 mg (0.27 mmol) of chloroacetic acid and 62 mg (0.32 mmol) of EDC-HCl were added thereto in sequence, and the resulting mixture was stirred at room temperature overnight. After the reaction was completed, dichloromethane was added thereto to dilute the mixture, and the mixture was washed with water and a 1% HCl aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the subject material. Amount obtained 4 mg (yield 5%).

1H-NMR (CDCl3, δ, ppm): 4.17 (2H, s), 5.46 (2H, s), 6.64 (1H, td), 7.31 (1H, d), 7.60 (1H, td), 7.64 (1H, dd), 7.80 (1H, dd), 8.32 (1H, d), 8.45 (1H, d)

MS: m/z=296 (M+H)

Synthetic Example P7: N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2-difluoroacetamide (Compound P238)

400 mg (4.26 mmol) of 2-aminopyridine was dissolved in 10 ml of anhydrous dichloromethane, 322 μl (490 mg, 5.11 mmol) of difluoroacetic acid, 982 mg (5.10 mmol) of EDC-HCl and 622 mg (5.11 mmol) of DMAP were added thereto, and the resulting mixture was stirred at room temperature for 61 hours. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twice with a 1% HCl aqueous solution, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 102 mg (yield 14%) of 2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide.

1H-NMR (CDCl3, δ, ppm): 6.03 (1H, t), 7.15 (1H, m), 7.78 (1H, td), 8.20 (1H, d), 8.34 (1H, dd), 8.72 (1H, brs)

100 mg (0.58 mmol) of the 2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by the aforementioned method was dissolved in 10 ml of anhydrous acetonitrile, 94 mg (0.58 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 5 ml of anhydrous acetonitrile and added thereto, and subsequently, 84 mg (0.63 mmol) of potassium carbonate was added thereto and the resulting mixture was heated and refluxed for 140 minutes. After the reaction was completed, the reaction solution was returned to room temperature to filter off insoluble materials, and the filtrate was concentrated under reduced pressure. Ether was added thereto to precipitate a solid, and thus the solid was collected and dried well to obtain the subject material. Amount obtained 63 mg (yield 37%).

1H-NMR (CDCl3, δ, ppm): 5.52 (2H, s), 5.90 (1H, t), 6.79 (1H, td), 7.33 (1H, d), 7.71 (1H, m), 7.77 (1H, dd), 7.85 (1H, dd), 8.45 (1H, d), 8.50 (1H, d)

13C-NMR (DMSO-d6, δ, ppm): 53.0, 111.0 (t), 115.2, 120.7, 124.7, 131.7, 140.6, 141.6, 143.2, 150.4, 150.9, 158.3, 169.4 (t)

MS: m/z=298 (M+H)

Synthetic Example P8: 2-chloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2-difluoroacetamide (Compound P239)

200 mg (2.13 mmol) of 2-aminopyridine was dissolved in 5 ml of dichloromethane, 491 mg (2.55 mmol) of EDC-HCl, 311 mg (2.55 mmol) of DMAP and 187 μl (2.23 mmol, 290 mg) of chlorodifluoroacetic acid were added thereto in sequence, and the resulting mixture was stirred overnight. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed with water and 1% hydrochloric acid, and then dried over anhydrous magnesium sulfate to obtain 105 mg (yield 24%) of 2-chloro-2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide.

1H-NMR (CDCl3, δ, ppm): 7.19 (1H, dd), 7.82 (1H, m), 8.18 (1H, d), 8.36 (1H, d), 9.35 (1H, brs)

53 mg (0.33 mmol) of 2-chloro-5-chloromethyl pyridine dissolved in 6 ml of anhydrous acetonitrile was added to 68 mg (0.33 mmol) of the 2-chloro-2,2-difluoro-N-(pyridin-2(1H)-ylidene)acetamide synthesized by the aforementioned method, and subsequently, 50 mg (0.36 mmol) of potassium carbonate was added thereto and the resulting mixture was heated and refluxed for 1 hours. After the reaction was completed, the reaction solution was returned to room temperature and then concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected and dried to obtain the subject material. Amount obtained 49 mg (yield 45%).

1H-NMR (CDCl3, δ, ppm): 5.56 (2H, s), 6.92 (1H, t), 7.33 (1H, d), 7.82 (1H, m), 7.91 (1H, dd), 8.02 (1H, d), 8.45 (1H, d), 8.48 (1H, d)

13C-NMR (CDCl3, δ, ppm): 53.8, 115.2, 120.1 (t), 122.1, 124.8, 139.0, 140.0, 142.3, 150.0, 151.9, 159.1, 159.1, 165.8 (t)

MS: m/z=332 (M+H)

Synthetic Example P9: 2,2,2-trichloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-acetamide (Compound P235)

70 mg (0.27 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the method described in another method of Synthetic Example P1 was dissolved in 4 ml of anhydrous dichloromethane, 94 μl (0.68 mmol, 68 mg) of triethylamine and 33 μg (0.27 mmol, 49 mg) of trichloroacetyl chloride were added thereto in sequence, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, water was added thereto to stop the reaction and liquid separation was performed with dichloromethane and water. The organic layer was washed once with water and twice with 1% hydrochloric acid, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected and dried to obtain the subject material. Amount obtained 61 mg (yield 62%).

1H-NMR (CDCl3, δ, ppm): 5.59 (2H, s), 6.86 (1H, t), 7.32 (1H, d), 7.78 (1H, td), 7.91 (2H, m), 8.43 (1H, d), 8.50 (1H, d)

MS: m/z=364 (M+H)

Synthetic Example P10: N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,3,3,3-pentafluoropropanamide (Compound P242)

300 mg (3.19 mmol) of 2-aminopyridine was dissolved in 15 ml of anhydrous dichloromethane, 919 mg (4.78 mmol) of EDC-HCl, 583 mg (4.78 mmol) of DMAP and 397 μl (628 mg, 3.83 mmol) of pentafluoropropionic acid were added thereto in sequence, and the resulting mixture was stirred at room temperature overnight. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twice with 1% hydrochloric acid, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 85 mg (yield 11%) of 2,2,3,3,3-pentafluoro-N-(pyridin-2(1H)-ylidene)propanamide.

52 mg (0.32 mmol) of 2-chloro-5-chloromethyl pyridine dissolved in 8 ml of anhydrous acetonitrile and 49 mg (0.35 mmol) of potassium carbonate were added to 77 mg (0.32 mmol) of the 2,2,3,3,3-pentafluoro-N-(pyridin-2(1H)-ylidene)propanamide obtained by the aforementioned method, and the resulting mixture was heated and refluxed for 11 hours. After the reaction was completed, the reaction solution was returned to room temperature to filter insoluble materials, and the filtrate was concentrated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=1:3) to obtain the subject material. Amount obtained 12 mg (yield 10%).

1H-NMR (CDCl3, δ, ppm): 5.56 (2H, s), 6.90 (1H, td), 7.32 (1H, d), 7.79 (2H, m), 7.84 (1H, d), 8.43 (1H, d), 8.56 (1H, d)

MS: m/z=366 (M+H)

Synthetic Example P11: N-[1-((2-chloropyrimidin-5-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound P243)

1.04 g (8.13 mmol) of 2-chloro-5-methyl pyrimidine was dissolved in 30 ml of carbon tetrachloride, 1.73 g (9.75 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed for 6 hours. After the reaction was completed, the reaction solution was returned to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 641 mg (yield 38%) of 5-bromomethyl-2-chloropyridine.

1H-NMR (CDCl3, δ, ppm): 4.42 (2H, s), 8.66 (2H, s)

104 mg (0.50 mmol) of the 5-bromomethyl-2-chloropyridine obtained by the aforementioned method was dissolved in 6 ml of anhydrous acetonitrile, 96 mg (0.50 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetoamide obtained by the method described in (1) of Synthetic Example P1 and 76 mg (0.55 mmol) of potassium carbonate were added thereto, and the resulting mixture was heated and refluxed for 1 hour. After the reaction was completed, the reaction solution was returned to room temperature to filter off insoluble materials, and the filtrate was concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected, washed with diethyl ether, and then dried under reduced pressure in a desiccator to obtain the subject material. Amount obtained 92 mg (yield 58%).

1H-NMR (CDCl3, δ, ppm): 5.54 (2H, s), 6.98 (1H, m), 7.87 (1H, m), 8.18 (1H, m), 8.48 (1H, m), 8.83 (2H, m)

13C-NMR (CDCl3, δ, ppm): 60.0, 115.6, 117.1 (q), 122.1, 127.5, 139.2, 142.9, 158.8, 160.3 (2C), 161.4, 163.8 (q)

MS: m/z=317 (M+H)

The compounds of P213 to P226, P228, P230, P232 to P234, P240 and P244 shown in the following Table were synthesized by the methods in accordance with Synthetic Examples P1 to P11.

TABLE 40

Com- IR (KBr, pound v, cm⁻¹) No. Ar R1a Y ¹H-NMR (CDCl3, δ, ppm) or MS P212 6-chloro- CF3 H 5.57 (2H, s), 6.92 m/z = 3-pyridyl (1H, td), 7.31 (1H, 316 d), 7.80 (1H, td), (M + H) 7.87 (1H, dd), 7.99 (1H, dd), 8.48 (2H, m) P213 2-chloro- CF3 H 5.61 (2H, s), 6.93 m/z = 5- (1H, dd), 7.68 (1H, s), 322 thiazolyl 7.83 (1H, td), 7.97 (M + H) (1H, d), 8.53 (1H, d) P214 6-chloro- OCH3 H 3.74 (3H, s), 5.40 m/z = 3-pyridyl (2H, s), 6.45 (1H, 278 td), 7.29 (1H, d), (M + H) 7.46 (2H, m), 7.73 (1H, dd), 8.12 (1H, dd), 8.40 (1H, d) P215 6-chloro- CF3 5- 5.53 (2H, s), 7.34 m/z = 3-pyridyl Cl (1H, d), 7.71 (1H, 350 dd), 7.87 (1H, dd), (M + H) 7.94 (1H, s), 8.49 (1H, d), 8.55 (1H, s) P216 6-chloro- CF3 5- 5.54 (2H, s), 7.34 m/z = 3-pyridyl F (1H, d), 7.70 (1H, m), 334 7.80 (1H, m), 7.88 (M + H) (1H, dd), 8.48 (1H, d), 8.64 (1H, m) P217 6-chloro- CF3 4- 5.49 (2H, s), 6.85 m/z = 3-pyridyl Cl (1H, dd), 7.35 (1H, 350 d), 7.76 (1H, dd), (M + H) 7.85 (1H, dd), 8.44 (1H, d), 8.62 (1H, s) P218 2-chloro- CF3 5- 5.56 (2H, s), 7.68 m/z = 5- Cl (1H, s), 7.74 (1H, 356 thiazolyl dd), 7.84 (1H, d), (M + H) 8.58 (1H, d) P219 2-chloro- CF3 5- 5.60 (2H, s), 7.69 m/z = 5- F (1H, s), 7.72 (1H, 340 thiazolyl td), 7.86 (1H, m), (M + H) 8.67 (1H, m) P220 2-chloro- CF3 4- 5.58 (2H, s), 6.90 m/z = 5- Cl (1H, d), 7.67 (1H, s), 356 thiazolyl 7.90 (1H, d), 8.61 (M + H) (1H, s) P221 6-chloro- CF3 3- 2.31 (3H, s), 5.50 m/z = 3-pyridyl Me (2H, s), 6.98 (1H, m), 330 7.34 (1H, d), 7.73 (M + H) (1H, dd), 7.77 (2H, m), 8.42 (1H, d) P222 6-chloro- CF3 4- 2.40 (3H, S), 5.49 m/z = 3-pyridyl Me (2H, s), 6.70 (1H, 330 dd), 7.32 (1H, d), (M + H) 7.70 (1H, d), 7.86 (1H, dd), 8.37 (1H, s), 8.43 (1H, d) P223 6-chloro- CF3 5- 2.29 (3H, s), 5.52 m/z = 3-pyridyl Me (2H, s), 7.32 (1H, d), 330 7.62 (1H, s), 7.65 (M + H) (1H, dd), 7.88 (1H, dd), 8.46 (1H, d), 8.50 (1H, d) P224 phenyl CF3 H 5.58 (2H, s), 6.81 m/z = (1H, m), 7.37 (4H, m), 281 7.77 (2H, m), 8.50 (M + H) (1H, d) P225 4- CF3 H 5.52 (2H, s), 6.85 m/z = chlorophen- (1H, m), 7.30 (2H, d), 315 yl 7.36 (2H, d), 7.75 (M + H) (1H, td), 7.84 (1H, d), 8.47 (1H, d) P226 3-pyridyl CF3 H 5.57 (2H, s), 6.86 m/z = (1H, m), 7.26-7.35 282 (2H, m), 7.78 (1H, (M + H) td), 7.86 (1H, m), 8.63 (2H, m), 8.67 (1H, d) P227 6-chloro- CF3 H 5.54 (2H, s), 6.89 m/z = 5-fluoro- (1H, td), 7.76 (1H, 334 3-pyridyl dd), 7.80 (1H, td), (M + H) 7.85 (1H, d), 8.29 (1H, d), 8.57 (1H, d) P228 6- CF3 H 5.62 (2H, s), 6.90 m/z = trifluro- (1H, t), 7.69 (1H, 350 methyl-3- d), 7.81 (1H, t), (M + H) pyridyl 7.88 (1H, d), 8.06 (1H, d), 8.56 (1H, d), 8.78 (1H, s) P229 6-fluoro- CF3 H 5.56 (2H, s), 6.89 m/z = 3-pyridyl (1H, td), 6.94 (1H, 300 d), 7.79 (1H, td), (M + H) 7.87 (1H, d), 8.03 (1H, m), 8.31 (1H, s), 8.54 (1H, d) P230 5,6- CF3 H 5.49 (2H, s), 6.89 m/z = dichloro- (1H, t), 7.79-7.90 350 3-pyridyl (2H, m), 8.04 (1H, (M + H) d), 8.37 (1H, d), 8.56 (1H, m)

TABLE 41

IR Com- (KBr, pound v, cm⁻¹) No. Ar R1a Y ¹H-NMR (CDCl3, δ, ppm) or MS P231 6-bromo- CF3 H 5.52 (2H, s), 6.88 m/z = 3-pyridyl (1H, t), 7.48 (1H, d), 360 7.78 (2H, m), 7.84 (M + H) (1H, d), 8.44 (1H, d), 8.53 (1H, d) P232 6-chloro- CF3 4- 5.52 (2H, s), 6.71 m/z = 3-pyridyl F (1H, m), 7.35 (1H, d), 334 7.86 (1H, dd), 7.94 (M + H) (1H, m), 8.33 (1H, dd), 8.44 (1H, d) P233 6-chloro- CF3 3- 5.53 (2H, s), 6.74 m/z = 3-pyridyl F (1H, m), 7.33 (1H, d), 334 7.87 (1H, dd), 8.07 (M + H) (1H, m), 8.29 (1H, dd), 8.45 (1H, d) P234 6-chloro- CHCl2 H 5.54 (2H, s), 6.02 m/z = 3-pyridyl (1H, s), 6.77 (1H, t), 330 7.32 (1H, m), 7.69 (M + H) (1H, m), 7.77 (1H, d), 7.89 (1H, m), 8.42 (1H, m), 8.49 (1H, s) P235 6-chloro- CCl3 H 5.59 (2H, s), 6.86 m/z = 3-pyridyl (1H, t), 7.32 (1H, d), 364 7.78 (1H, td), 7.91 (M + H) (2H, m), 8.43 (1H, d), 8.50 (1H, d) P236 6-chloro- CH2Cl H 4.17 (2H, s), 5.46 m/z = 3-pyridyl (2H, s), 6.64 (1H, 296 td), 7.31 (1H, d), (M + H) 7.60 (1H, td), 7.64 (1H, dd), 7.80 (1H, dd), 8.32 (1H, d), 8.45 (1H, d) P238 6-chloro- CHF2 H 5.52 (2H, s), 5.90 m/z = 3-pyridyl (1H, t), 6.79 (1H, 298 td), 7.33 (1H, d), (M + H) 7.71 (1H, m), 7.77 (1H, dd), 7.85 (1H, dd), 8.45 (1H, d), 8.50 (1H, d) P239 6-chloro- CF2Cl H 5.56 (2H, s), 6.92 m/z = 3-pyridyl (1H, t), 7.33 (1H, d), 332 7.82 (1H, m), 7.91 (M + H) (1H, dd), 8.02 (1H, d), 8.45 (1H, d), 8.48 (1H, d) P240 6-chloro- CH2ClBr H 5.53 (1H, d), 5.58 m/z = 3-pyridyl (1H, d), 6.06 (1H, s), 374 6.76 (1H, td), 7.32 (M + H) (1H, d), 7.69 (1H, m), 7.70 (1H, m), 7.90 (1H, dd), 8.40 (1H, d), 8.50 (1H, d) P241 6-chloro- CHBr2 H 5.56 (2H, s), 5.99 m/z = 3-pyridyl (1H, s), 6.78 (1H, 418 td), 7.33 (1H, d), (M + H) 7.69 (1H, td), 7.76 (1H, dd), 7.93 (1H, dd), 8.39 (1H, d), 8.50 (1H, d) P242 6-chloro- CF2CF3 H 5.56 (2H, s), 6.90 m/z = 3-pyridyl (1H, td), 7.32 (1H, 366 d), 7.79 (2H, m), 7.84 (M + H) (1H, d), 8.43 (1H, d), 8.56 (1H, d) P243 2-chloro- CF3 H 5.54 (2H, s), 6.98 m/z = 5- (1H, m), 7.87 (1H, m), 317 pyrimi- 8.18 (1H, m), 8.48 (M + H) dinyl (1H, m), 8.83 (2H, m) P244 6-chloro- CH2Br H 4.17 (2H, s), 5.46 3-pyridyl (2H, s), 6.63 (1H, td), 7.31 (1H, d), 7.60 (1H, td), 7.65 (1H, dd), 7.80 (1H, dd), 8.32 (1H, d), 8.47 (1H, d)

Synthetic Example 1: 2,2-difluoro-N-[1-((6-fluoropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]acetamide (Compound 3-3)

(1) 400 mg (4.26 mmol) of 2-aminopyridine was dissolved in 10 ml of anhydrous dichloromethane, 322 μl (490 mg, 5.11 mmol) of difluoroacetic acid, 982 mg (5.10 mmol) of EDC-HCl and 622 mg (5.11 mmol) of DMAP were added thereto, and the resulting mixture was stirred at room temperature for 61 hours. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twice with a 1% HCl aqueous solution, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 102 mg (yield 14%) of 2,2-difluoro-N-(pyridin-2(1H)-ylidene) acetamide.

1H-NMR (CDCl3, δ, ppm): 6.03 (1H, t), 7.15 (1H, m), 7.78 (1H, td), 8.20 (1H, d), 8.34 (1H, dd), 8.72 (1H, brs)

(2) 128 mg (0.75 mmol) of 5-bromomethyl-2-fluoropyridine was dissolved in 3 ml of anhydrous DMF, 116 mg (0.68 mmol) of 2,2-difluoro-N-[pyridin-2(1H)-ylidene]acetamide was dissolved in 3 ml of anhydrous DMF and added thereto, and subsequently, 103 mg (0.75 mmol) of potassium carbonate was added thereto and the resulting mixture was stirred at 65° C. for 2 hours. After the reaction was completed, the reaction solution was returned to room temperature, and ethyl acetate and water were added thereto to perform liquid separation. The organic layer was washed with 1% hydrochloric acid, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. A small amount of hexane and diethyl ether were added thereto to precipitate crystals, and thus the crystals were collected and dried to obtain the subject material. Amount obtained 50 mg (yield 26%).

Synthetic Example 2: N-[1-((6-chloropyridin-3-yl)methyl)pyrimidin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound 190-2)

(1) 300 mg (1.86 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 6 ml of anhydrous DMF, 118 mg (1.24 mmol) of 2-aminopyrimidine was added thereto, and the resulting mixture was stirred at 80° C. for 8 hours. After the reaction was completed, the reaction solution was returned to room temperature to distill off DMF under reduced pressure. Diethyl ether was added thereto, and thus crystallization was occurred on the wall surface of an eggplant flask. Diethyl ether was removed by decantation and dried well to obtain 1-((6-chloropyridin-3-yl)methyl)pyrimidin-2(1H)-imine hydrochloride. Amount obtained 107 mg (yield 34%)

(2) 71 mg (0.27 mmol) of the 1-((6-chloropyridin-3-yl)methyl)pyrimidin-2(1H)-imine hydrochloride obtained by the aforementioned method was suspended in 5 ml of anhydrous dichloromethane, 114 μl (0.83 mmol, 83 mg) of triethylamine and 53 μl (0.38 mmol) of trifluoroacetic anhydride were added thereto in sequence, and the resulting mixture was stirred at room temperature for 2 hours. After the reaction was completed, dichloromethane and water were added to the reaction solution to perform liquid separation, and the organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. A small amount of diethyl ether was added thereto to precipitate crystals, and thus the crystals were collected, washed with a small amount of diethyl ether, and then dried to obtain the subject material. Amount obtained 24 mg (yield 28%).

Synthetic Example 3: 2,2,2-trifluoroethyl-[1-((6-chloropyridin-3-yl)methyl)pyridin-(2H)-ylidene]carbamate (Compound 1-17)

(1) 3.00 g (18.6 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 20 ml of anhydrous DMF, 1.75 g (18.6 mmol) of 2-aminopyridine was added thereto, and the resulting mixture was stirred at 80° C. for 8 hours and at room temperature for 5 hours. After the reaction was completed, DMF was distilled off under reduced pressure, acetonitrile was added thereto to precipitate a solid, and the solid was collected, washed well with acetonitrile and then dried to obtain 2.07 g (yield 44%) of 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride.

1H-NMR (DMSO-d6, δ, ppm): 5.65 (2H, s), 6.96 (1H, t), 7.23 (1H, m), 7.57 (1H, d), 7.80 (1H, m), 7.91 (1H, m), 8.28 (1H, m), 8.49 (1H, d)

(2) 10 ml of anhydrous acetonitrile was added to 150 mg (0.66 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the aforementioned method, 177 mg (0.66 mmol) of 4-nitrophenyl (2,2,2-trifluoroethyl)carbamate and 200 mg (1.46 mmol) of potassium carbonate were added, and the resulting mixture was stirred at 50° C. for 2 hours. After the reaction was completed, the reaction solution was returned to room temperature to filter off insoluble materials, and the filtrate was concentrated under reduced pressure. Dichloromethane and water were added thereto to perform liquid separation, and the organic layer was washed with 1% hydrochloric acid, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. A small amount of diethyl ether was added thereto to precipitate crystals, and thus the crystals were collected and dried well to obtain the subject material. Amount obtained 48 mg (yield 21%).

Synthetic Example 4: N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (Compound 1-20)

(1) 25 g (270 mmol) of 2-aminopyridine was dissolved in 200 ml of anhydrous dichloromethane, 41 ml (30 g, 300 mmol) of triethylamine was added thereto, and the mixture was cooled to 0° C. 38 ml (57 g, 270 mmol) of anhydrous trifluoroacetic acid was added dropwise thereto over 15 minutes, and the resulting mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was injected into about 100 ml of iced water, and the mixture was stirred for 10 minutes. The mixture was transferred to a separatory funnel to perform liquid separation, and the organic layer was washed twice with 150 ml of water and twice with 150 ml of a 1% HCl aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 36 g (yield 71%) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene) acetamide.

1H-NMR (CDCl3, δ, ppm): 7.20 (1H, m), 7.83 (1H, m), 8.20 (1H, d), 8.35 (1H, d), 10.07 (1H, brs)

13C-NMR (CDCl3, δ, ppm): 115.3, 115.5 (q), 121.6, 139.1, 147.9, 149.5, 155.3 (q)

(2) 20 g (126 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 200 ml of anhydrous acetonitrile, 24 g (126 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by the above-described method and 21 g (151 mmol) of potassium carbonate were added thereto, and the resulting mixture was heated and refluxed for 6 hours, and then stirred at room temperature for 10 hours. After the reaction was completed, the reaction solution was filtered and the filtrate was concentrated under reduced pressure. Diethyl ether was added thereto for crystallization, and the crystals thus obtained were collected and washed well with diethyl ether and water. The crystals thus obtained were dried under reduced pressure at 60° C. for 1 hour to obtain N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (P212). Amount obtained 26 g (yield 66%).

1H-NMR (CDCl3, δ, ppm): 5.57 (2H, s), 6.92 (1H, td), 7.31 (1H, d), 7.80 (1H, td), 7.87 (1H, dd), 7.99 (1H, dd), 8.48 (2H, m)

13C-NMR (CDCl3, δ, ppm): 53.8, 115.5, 117.2 (q), 122.1, 124.7, 130.0, 139.2, 140.0, 142.5, 149.7, 151.8, 158.9, 163.5 (q)

MS: m/z=316 (M+H)

(3) 180 ml of toluene was added to 16.3 g (36.7 mmol) of phosphorus pentasulfide, 6.72 g (63.4 mmol) of sodium carbonate was added thereto and the resulting mixture was stirred at room temperature for 5 minutes. 20.0 g (63.4 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide obtained by the above-described method was added thereto, and the resulting mixture was stirred at 50° C. for 19 hours. 150 ml of ethyl acetate was added to the reaction solution, the resulting mixture was stirred at 50° C. for 10 minutes, then insoluble materials were filtered off, and 250 ml of ethyl acetate was used to wash the mixture. The mixture was transferred to a separatory funnel, washed therein with 300 ml of a saturated sodium bicarbonate water and 200 ml of a saturated saline solution, and then concentrated under reduced pressure. 200 ml of water was added thereto to precipitate crystals. The mixture was stirred at room temperature for 1 hour, and then the crystals were collected, subjected to slurry washing twice with 150 ml of water and twice with 150 ml of hexane, and dried at 60° C. under reduced pressure for 2 hours to obtain the subject material. Amount obtained 19.5 g (yield 94%).

1H-NMR (CDCl3, δ, ppm): 5.48 (2H, s), 7.12 (1H, td), 7.34 (1H, d), 7.77 (1H, dd), 7.96 (1H, m), 8.05 (1H, dd), 8.45 (1H, d), 8.56 (1H, d)

MS: m/z=332 (M+H)

Synthetic Example 5: N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-methylacetimidamide (Compound 1-42)

150 mg (0.45 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (1-20) synthesized by the method in Synthetic Example 4 was dissolved in 5 ml of methanol, 105 μl (42 mg, 1.36 mmol) of methylamine (40% methanol solution) and 124 mg (0.45 mmol) of silver carbonate were added thereto, and the resulting mixture was stirred at 50° C. for 1 hour. After the reaction was completed, the reaction solution was returned to room temperature and subjected to suction filtration by using celite to remove insoluble materials. Ethyl acetate and water were added thereto to perform liquid separation, and the organic layer was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and purified with silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the subject material. Amount obtained 81 mg (yield 56%).

Synthetic Example 6: N′-(aryloxy)-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetimidamide (Compound 1-507)

30 mg (0.09 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (1-20) synthesized by the method in Synthetic Example 4 was dissolved in 5 ml of ethanol, 50 mg (0.45 mmol) of 0-ally hydroxylamine hydrochloride, 62 μl (0.45 mmol, 45 mg) of triethylamine and 25 mg (0.09 mmol) of silver carbonate were added thereto, and the resulting mixture was stirred at 50° C. for 5 hours and 20 minutes. After the reaction was completed, the reaction solution was returned to room temperature to filter off insoluble materials. The filtrate was concentrated under reduced pressure to perform liquid separation with ethyl acetate and 1% hydrochloric acid, then the ethyl acetate layer was washed with a saturated saline solution, and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The ethyl acetate layer was purified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane:ethyl acetate=1:1) to obtain the subject material. Amount obtained 15 mg (yield 45%).

Synthetic Example 7: N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide (Compound 1-499)

25 ml of ethanol was added to 1.00 g (3.00 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (1-20) 1 synthesized by the method in Synthetic Example 4, 1.04 g (15.0 mmol) of hydroxylamine hydrochloride and 2.00 ml (1.50 g, 15.0 mmol) of triethylamine were added thereto in sequence, and the resulting mixture was stirred at 50° C. for 21.5 hours. After the reaction was completed, ethyl acetate and 1% hydrochloric acid were added to the reaction solution to perform liquid separation, and the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The organic layer was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the subject material. Amount obtained 625 mg (yield 63%).

Synthetic Example 8: N-(benzoyloxy)-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetimidamide (Compound 1-519)

30 mg (0.09 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide (1-499) synthesized by the method in Synthetic Example 7 was dissolved in 3 ml of anhydrous acetonitrile, 24 μl (17 mg, 0.17 mmol) of triethylamine and 20 μg (22 mg, 0.17 mmol) of benzoyl chloride were added thereto in sequence, and the resulting mixture was stirred at room temperature for 10 minutes. After the reaction was completed, ethyl acetate and 1% hydrochloric acid were added to the reaction solution to perform liquid separation, and the organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The organic layer was purified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane:ethyl acetate=1:1) to obtain the subject material. Amount obtained 26 mg (yield 67%).

Synthetic Example 9: N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-((propylcarbamoyl)oxy)acetimidamide (Compound 1-534)

5 ml of anhydrous acetonitrile was added to 11 mg (0.13 mmol) of normal propyl isocyanate, 40 mg (0.12 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide (1-499) synthesized by the method in Synthetic Example 7 and 4 mg (0.04 mmol) of potassium-t-butoxide were added thereto, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and ethyl acetate and a saturated saline solution were added thereto to perform liquid separation. The ethyl acetate layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure and purified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane:ethyl acetate=1:3) to obtain the subject material. Amount obtained 16 mg (yield 32%).

Synthetic Example 10: Diisopropyl 1-((6-chloropyridin-3-yl)methyl)pyridyn-2(1H)-ylidenphospholamide trithioate (Compound 1-702)

4.0g (15.7 mmol) of 1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-imine hydrochloride obtained by the above-described method was suspended in 24.6 ml of dichloromethane, and under ice-cooling 1.35 ml of phosphorpus trichloride over 10 mins, following 3.16g (31.2 mmol) of triethylamine dissolved in 37 ml of dichloromethane was added thereto. After the mixture was stirred for 2 hours at room temperature, 499 mg (15.6 mmol) of sulfur was added to the mixture, and the mixture was stirred over night at room temperature. Under ice-cooling 3.16g (31.2 mmol) of triethylamine, following 2.38g (31.2 mmol) of 2-propanethiol dissolved in 10 ml of dichloromethane were added to the mixture, additionary the mixture was stirred for a day. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and was extracted by 100 ml of diethylether twice. The ether solution was concentrated under reduced pressure, and 2.49g of cruede compounds was obtained. 186 mg of crude compound was purified by a TLC plate (5 sheets of 0.5 mm plate, evolved with ethyl acetate) to obtain the subject material (47 mg. yield 9%) and (1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene)phosphoramidothioic dichloride (19 mg. yield 5%).

(1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene) phosphoramidothioic dichloride Synthetic Example 11: N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-1,1,1-trifluoromethanesulfinamide (Compound1-703)

330 mg (2 mmol) of sodium trifluoromethanesulfonate was added by 2 ml of ethylacetate and 154 mg (1 mmol) of phosphorus oxychloride and stirred for 5 min at room temperature. And 220 mg (0.86 mmol) of 1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-imine hydrochloride obtained by the above-described method was added to the mixture, and stirred for 2 hours. After the reaction was completed, the reaction mixture was purified by silica-gel column chromatography (eluent ethylacetate:hexane=1:1) to obtain the subject material (115 mg. yield 39%)

The compounds shown in the following Table were prepared by the method in accordance with Synthetic Examples 1 to 11.

TABLE 42 Com- Reaction pound Base and the temperature, Method Yield No. Raw material 1 Raw material 2 like Solvent Time (Table) (%) 266-2 69 mg (0.43 mmol) of 84 mg (0.43 mmol) 71 mg (0.52 mmol) Acetonitrile reflux, 20 h A 32 2-chloro-5- of 2,2,2- of (chloromethyl)pyridine trifluoro-N- potassium (1,3,4- carbonate thiadiazol- 2(3H)- ylidene))acetamide 444-2 56 mg (0.41 mmol) of 66 mg (0.34 mmol) 56 mg (0.41 mmol) Acetonitrile reflux, 20 h A 21 2-chloro-5- of 2,2,2- of (chloromethyl)thiazole trifluoro-N- potassium (1,3,4- carbonate thiadiazol- 2(3H)- ylidene))acetamide 190-2 71 mg (0.27 mmol) of 53 μl (0.38 mmol) 53 μl (0.38 mmol) Dichloromethane Room B 28 1-((6-chloropyridin- of of temperature, 3- anhydrous triethylamine 1 h yl)methyl)pyrimidin- trifluoroacetic 2(1H)-imine acid hydrochloride 201-2 120 mg (0.47 mmol) of 99 μl (0.71 mmol) 160 μl (1.17 mmol) Dichloromethane Room B 11 1-((6-chloropyridin- of of temperature, 3-yl)methyl)pyrazin- anhydrous triethylamine 30 min 2(1H)-imine trifluoroacetic hydrochloride acid 223-2 530 mg (2.07 mmol) of 2- 390 μl (2.79 mmol) 537 μl (2.79 mmol) Dichloromethane Room B 14 chloro-2-((6- of anhydrous of temperature, chloropyridin-3- trifluoroacetic acid triethylamine 2 h yl)methyl)pyridazin- 3(2H)-imine hydrochloride 146-2 113 mg (0.70 mmol) of 2- 145 mg (0.70 mmol) 116 mg (0.84 mmol) Acetonitrile reflux, 13 h A 15 chloro-5- of 2,2,2-trifluoro- of (chloromethyl)pyridine N-(3-hydroxypyridin- potassium 2(1H)- carbonate ylidene))acetamide 224-2 190 mg (0.73 mmol) of 2- 168 μl (1.20 mmol) 220 μl (1.60 mmol) Dichloromethane Room B 16 ((2-chlorothiazol-5- of anhydrous of temperature, yl)methyl)pyridazin- trifluoroacetic acid triethylamine 5 min 3(2H)-imine hydrochloride 102-2 116 mg (0.72 mmol) of 2- 155 mg (0.72 mmol) 109 mg (0.79 mmol) Acetonitrile reflux, 8 h A 22 chloro-5- of N-(3- of (chloromethyl)pyridine cyanopyridin-2(1H)- potassium ylidene))2,2,2- carbonate trifluoroacetamide 212-2 59 mg (0.37 mmol) of 2- 70 mg (0.37 mmol) of 55 mg (0.40 mmol) Acetonitrile reflux, 7 h A 32 chloro-5- 2,2,2-trifluoro-N- of (chloromethyl)pyridine (pyrimidin-4(3H)- potassium ylidene))acetamide carbonate   1-20 20.0 g (63.4 mmol) of N-[1- 16.3 g (36.7 mmol) of 6.72 mg Toluene 50° C., D 94 ((6-chloropyridin-3- phosphorus pentasulfide (63.4 mmol) 19 h yl)methyl)pyridin-2(1H)- of sodium ylidene]-2,2,2- carbonate trifluoroacetamide  12-2 78 mg (0.38 mmol) of 2- 73 mg (0.38 mmol) of 2,2,2- 58 mg (0.42 mmol) Acetonitrite reflux, A 44 chloro-4- trifluoro-N-(pyridin-2(1H)- of 3.5 h (bromomethyl)pyridine ylidene))acetamide potassium carbonate 213-2 79 mg (0.47 mmol) of 2- 90 mg (0.47 mmol) of 2,2,2- 72 mg (0.52 mmol) Acetonitrile reflux, A 42 chloro-5- trifluoro-N-(pyrimidin- of 12 h (chloromethyl)thiazole 4(3H)-ylidene))acetamide potassium carbonate   1-17 150 mg (0.66 mmol) of 1-[(6- 177 mg (0.66 mmol) of 4- 200 mg Acetonitrile 50° C., C 21 chloropyridin-3- nitrophenyl(2,2,2- (1.46 mmol) 2 h yl)methyl]pyridin-2(1H)- trifluoroethyl)carbamate of imine hydrochloride potassium carbonate   1-18 150 mg (0.66 mmol) of 1-[(6- 184 mg (0.66 mmol) of 4- 200 mg Acetonitrile 50° C., C 30 chloropyridin-3- nitrophenyl(1,1,1- (1.46 mmol) 2 h yl)methyl]pyridin-2(1H)- trifluoropropan-2- of imine hydrochloride yl)carbamate potassium carbonate   1-19 150 mg (0.66 mmol) of 220 mg (0.66 mmol) of 200 mg (1.46 mmol) Acetonitrile 50° C., 3 h C 27 1-[(6-chloropyridin-3- 1,1,1,3,3,3- of potassium yl)methyl]pyridin- hexafluoropropan-2- carbonate 2(1H)-imine yl(4- hydrochloride nitrophenyl)carbamate  7-2 116 mg (0.72 mmol) of 137 mg (0.72 mmol) of 110 mg (0.80 mmol) Acetonitrile reflux, 5 h A 49 2-chloro-5- 2,2,2-trifluoro-N- of potassium (chloromethyl)pyrazine (pyridin-2(1H)- carbonate ylidene))acetamide   1-13 200 mg (0.78 mmol) of 103 μl (1.17 mmol) of EDC- Dichloromethane Room B 21 1-[(6-chloropyridin-3- 2,2,2- HCl 225 m g(1.17 mmol), temperature, yl)methyl]pyridin- trifluoropropionic DMAP 238 mg 12 h 2(1H)-imine acid (1.95 mmol) hydrochloride

TABLE 43 Reaction Compound Base and temperature, Method Yield No. Raw material 1 Raw material 2 the like Solvent Time (Table) (%) 168-2  273 mg (1.70 mmol) of 2- 350 mg (1.70 mmol) 248 mg DMF 65° C., 2 h A 15 chloro-5- of 2,2,2-trifluoro- (1.80 mmol) (chloromethyl)pyridine N-(5- of hydroxypyridin- potassium 2(1H)- carbonate ylidene))acetamide  1-21 23 mg (0.077 mmol) of N- 41 mg (0.092 mmol) 10 mg THF Room D 49 [1-((6-chloropyridin-3- of phosphorus (0.092 mmol) temperature, yl)methyl)pyridin-2(1H)- pentasulfide of 2 h ylidene]-2,2- sodium difluoroacetamide carbonate  3-20 30 mg (0.10 mmol) of N- 49 mg (0.11 mmol) 12 mg THF Room D 49 [1-((6-fluoropyridin-3- of phosphorus (0.11 mmol) temperature, yl)methyl)pyridin-2(1H)- pentasulfide of 3 h ylidene]-2,2,2- sodium trifluoroacetamide carbonate  4-20 30 mg (0.083 mmol) of N- 41 mg (0.09 mmol) 10 mg THF Room D 61 [1-((6-bromopyridin-3- of phosphorus (0.09 mmol) temperature, yl)methyl)pyridin-2(1H)- pentasulfide of 3 h ylidene]-2,2,2- sodium trifluoroacetamide carbonate 3-3 116 mg (0.72 mmol) of 2- 116 mg (0.68 mmol) 110 mg Acetonitrile reflux, A 27 fluoro-5- of 2,2-difluoro-N- (0.80 mmol) 6 h (bromomethyl)pyridine (pyridin-2(1H)- of ylidene))acetamide potassium carbonate 4-3 50 mg (0.20 mmol) of 2- 35 mg (0.20 mmol) of 33 mg Acetonitrile reflux, A 53 bromo-5- 2,2-difluoro-N- (0.24 mmol) 6 h (bromomethyl)pyridine (pyridin-2(1H)- of ylidene))acetamide potassium carbonate 5-5 46 mg (0.21 mmol) of 5- 50 mg (0.21 mmol) of 35 mg Acetonitrile reflux, A 26 (bromomethyl)-2-chloro- 2,2,3,3,3- (0.25 mmol) 2 h 3-fluoropyridine pentafluoro-N- of (pyridin-2(1H)- potassium ylidene))propanamide carbonate 6-5 43 mg (0.21 mmol) of 5- 50 mg (0.21 mmol) of 35 mg Acetonitrile reflux, A 21 (bromomethyl)-2- 2,2,3,3,3- (0.25 mmol) 2 h chloropyrimidine pentafluoro-N- of (pyridin-2(1H)- potassium ylidene))propanamide carbonate  1-22 37 mg (0.11 mmol) of 2- 49 mg (0.11 mmol) of 12 mg THF Room D 31 chloro-N-[1-((6- phosphorus (0.11 mmol) temperature, 4 h chloropyridin-3- pentasulfide of yl)methyl)pyridin-2(1H)- sodium ylidene]-2,2- carbonate difluoroacetamide  1-23 31 mg (0.085 mmol) of N- 38 mg (0.085 mmol) 9 mg THF Room D 59 [1-((6-chloropyridin-3- of phosphorus (0.0854 mmol) temperature, 4 h yl)methyl)pyridin-2(1H)- pentasulfide of ylidene]-2,2,3,3,3- sodium pentafluoropropanamide carbonate  5-20 36 mg (0.11 mmol) of N- 49 mg (0.11 mmol) of 12 mg THF Room D 100 [1-((6-chloro-5- phosphorus (0.11 mmol) temperature, fluoropyridin-3- pentasulfide of 4 h yl)methyl)pyridin-2(1H)- sodium ylidene]-2,2,2- carbonate trifluoroacetamide 5-3 65 mg (0.29 mmol) of 5- 50 mg (0.29 mmol) of 48 mg Acetonitrile reflux, 3 h A 38 (bromomethyl)-2-chloro- 2,2-difluoro-N- (0.35 mmol) 3-fluoropyridine (pyridin-2(1H)- of ylidene))acetamide potassium carbonate 6-3 60 mg (0.29 mmol) of 5- 50 mg (0.29 mmol) of 48 mg Acetonitrile reflux, 3 h A 37 (bromomethyl)-2- 2,2-difluoro-N- (0.35 mmol) chloropyrimidine (pyridin-2(1H)- of ylidene))acetamide potassium carbonate 8-2 73 mg (0.45 mmol) of 3- 97 mg (0.51 mmol) of 83 mg DMF 65° C., 3 h A 32 chloro-6- 2,2,2-trifluoro-N- (0.60 mmol) (chloromethyl)pyridazine (pyridin-2(1H)- of ylidene))acetamide potassium carbonate 5-4 54 mg (0.24 mmol) of 5- 50 mg (0.24 mmol) of 41 mg Acetonitrile reflux, 6 h A 51 (bromomethyl)-2-chloro- 2-chloro-2,2- (0.30 mmol) 3-fluoropyridine difluoro-N-(pyridin- of 2(1H)- potassium ylidene))acetamide carbonate 4-4 60 mg (0.24 mmol) of 2- 50 mg (0.24 mmol of 41 mg Acetonitrile reflux, 6 h A 48 bromo-5- 2-chloro-2,2- (0.30 mmol) bromomethylpyridine difluoro-N-(pyridin- of 2(1H)- potassium ylidene))acetamide carbonate 6-4 49 mg (0.24 mmol) of 5- 50 mg (0.24 mmol) of 41 mg Acetonitrile reflux, 6 h A 55 (bromomethyl)-2- 2-chloro-2,2- (0.30 mmol) chloropyrimidine difluoro-N-(pyridin- of 2(1H)- potassium ylidene))acetamide carbonate 4-5 65 mg (0.26 mmol) of 2- 50 mg (0.26 mmol) of 41 mg Acetonitrile reflux, 2 h A 8 bromo-5- 2,2,3,3,3- (0.30 mmol) bromomethylpyridine pentafluoro-N- of (pyridin-2(1H)- potassium ylidene))propanamide carbonate

TABLE 44 Reaction Compound Base and the temperature, Method Yield No. Raw material 1 Raw material 2 like Solvent Time (Table) (%) 2-20 70 mg (0.22 mmol) of N- 107 mg (0.24 mmol) 25 mg (0.24 mmol) THF Room D 11 [1-((2-chlorothiazol-5- of phosphorus of temperature, yl)methyl)pyridin- pentasulfide sodium 4 h 2(1H)-ylidene]-2,2,2- carbonate trifluoroacetamide 10-20  130 mg (0.37 mmol) of 181 mg (0.41 mmol) 43 mg (0.41 mmol) THF Room D 93 2,2,2-trifluoro-N-[1- of phosphorus of temperature, ((6- pentasulfide sodium 4 h trifluoromethyl)pyridin- carbonate 3-yl)methyl)pyridin- 2(1H)-ylidene]- acetamide 3-4  110 mg (0.58 mmol) of 105 mg (0.51 mmol) 103 mg (0.75 mmol) DMF 65° C., 2 h A 63 2-fluoro-5- of 2-chloro-2,2- of (bromomethyl)pyridine difluoro-N- potassium (pyridin-2(1H)- carbonate ylidene))acetamide 3-5  110 mg (0.58 mmol) of 139 mg (0.58 mmol) 88 mg (0.63 mmol) DMF 65° C. 2 h A 22 2-fluoro-5- of 2,2,3,3,3- of (bromomethyl)pyridine pentafluoro-N- potassium (pyridin-2(1H)- carbonate ylidene)propanamide 11-20  40 mg (0.15 mmol) of 65 mg (0.11 mmol) 16 mg (0.15 mmol) THF Room D 53 2,2,2-trifluoro-N-[1- of phosphorus of temperature, ((tetrahydrofuran-3- pentasulfide sodium 4 h yl)methyl)pyridin- carbonate 2(1H)-ylidene]acetamide 1-14 200 mg (0.78 mmol) of 76 μl (0.94 mmol) 32 μl (0.23 mmol) Acetonitrile reflux, 1 h B 28 1-[(6-chloropyridin-3- of acrylic acid of yl)methyl]pyridin- chloride triethylamine 2(1H)-imine hydrochloride 1-37 78 mg (0.28 mmol) of N- 125 mg (0.28 mmol) 30 mg (0.28 mmol) THF Room D 21 [1-((6-chloropyridin-3- of phosphorus of temperature, yl)methyl)pyridin- pentasulfide sodium 2 h 2(1H)-ylidene]- carbonate propionamide 1-39 180 mg (0.96 mmol) of 341 mg (0.75 mmol) 102 mg (0.96 mmol) THF Room D 29 N-[1-((6-chloropyridin- of phosphorus of temperature, 3-yl)methyl)pyridin- pentasulfide sodium 2 h 2(1H)-ylidene]- carbonate isobutyramide 1-40 54 mg (0.19 mmol) of N- 54 mg (0.19 mmol) 20 mg (0.19 mmol) THF Room D 12 [1-((6-chloropyridin-3- of phosphorus of temperature, yl)methyl)pyridin- pentasulfide sodium 2 h 2(1H)-ylidene]- carbonate cyclopropane carboxyamide 1-15 200 mg (0.78 mmol) of 1- 83 mg (0.94 mmol) 320 μl (2.34 mmol) Acetonitrile reflux, 5 h B 19 [(6-chloropyridin-3- of propyol of yl)methyl]pyridin-2(1H)- oxychloride triethylamine imine hydrochloride 1-35 26 mg (0.074 mmol) of N- 26 mg (0.06 mmol) 8 mg (0.074 mmol) THF Room D 23 [1-((6-chloropyridin-3- of phosphorus of temperature, yl)methyl)pyridin-2(1H)- pentasulfide sodium 1.5 h ylidene]-3- carbonate phyenylpropanamide  1-501 100 mg (0.30 mmol) of N- 145 mg (1.50 mmol) 205 μl (1.50 mmol) Ethanol 50° C., 19.5 h F 14 [1-((6-chloropyridin-3- of O-ethyl of yl)methyl)pyridin-2(1H)- hydroxylamine triethylamine ylidene]-2,2,2- hydrochloride trifluoroethanethioamide  1-499 1.00 g (3.00 mmol) of N- 1.04 g (15.0 mmol) 2.00 ml (15.0 mmol) Ethanol 50° C., 21 h F 63 [1-((6-chloropyridin-3- of hydroxylamine of yl)methyl)pyridin-2(1H)- hydrochloride triethylamine ylidene]-2,2,2- trifluoroethanethioamide  1-510 1.00 g (3.00 mmol) of N- 239 mg (1.50 mmol) 205 μl (1.50 mmol) Ethanol 50° C., 19.5 h F 20 [1-((6-chloropyridin-3- of O-benzyl of yl)methyl)pyridin-2(1H)- hydroxylamine triethylamine ylidene]-2,2,2- hydrochloride trifluoroethanethioamide  1-511 30 mg (0.09 mmol) of N- 20 μl (0.28 mmol) 38 μl (0.28 mmol) Acetonitrile Room G 72 [1-((6-chloropyridin-3- of acetyl chloride of temperature, yl)methyl)pyridin- triethylamine 15 min 2(1H)-ylidene]-2,2,2- trifluoro-N′- hydroxyacetimidamide

TABLE 45 Com- Reaction pound Base and the temperature, Method Yield No. Raw material 1 Raw material 2 like Solvent Time (Table) (%) 1-519 30 mg (0.09 mmol) of 20 μl (0.17 mmol) 24 μl (0.17 mmol) Acetonitrile Room G 67 N-[1-((6- of of temperature, chloropyridin-3- benzoyl triethylamine 10 min yl)methyl)pyridin- chloride 2(1H)-ylidene]-2,2,2- trifluoro-N′- hydroxyacetimidamide 1-523 30 mg (0.09 mmol) of 20 μl (0.26 mmol) 36 μl (0.26 mmol) Acetonitrile Room G 49 N-[1-((6- of methyl of temperature, chloropyridin-3- chloroformate triethylamine 20 min yl)methyl)pyridin- 2(1H)-ylidene]-2,2,2- trifluoro-N′- hydroxyacetimidamide 1-528 30 mg (0.09 mmol) of 20 μl (0.18 mmol) 25 μl (0.18 mmol) Acetonitrile Room G 100 N-[1-((6- of of temperature, chloropyridin-3- methanesulfonyl triethylamine 20 min yl)methyl)pyridin- chloride 2(1H)-ylidene]-2,2,2- trifluoro-N′- hydroxyacetimidamide 1-531 30 mg (0.09 mmol) of 28 mg (0.15 mmol) 21 μl (0.15 mmol) Acetonitrile Room G 100 N-[1-((6- of 4- of temperature, chloropyridin-3- methylbenzenesufonyl triethylamine 12 h yl)methyl)pyridin- chloride 2(1H)-ylidene]- 2,2,2-trifluoro-N′- hydroxyacetimidamide 1-507 30 mg (0.09 mmol) of 50 mg (0.45 mmol) 62 μl (0.45 mmol) Ethanol 50° C., 5 h F 45 N-[1-((6- of O- of chloropyridin-3- allyl triethylamine, yl)methyl)pyridin- hydroxylamine 25 mg (0.09 mmol) 2(1H)-ylidene]- hydrochloride of 2,2,2- silver trifluoroethanethioamide carbonate 1-516 30 mg (0.09 mmol) of 20 μl (0.25 mmol) 34 μl (0.25 mmol) Acetonitrile Room G 64 N-[1-((6- of of temperature, chloropyridin-3- acryloyl triethylamine 20 min yl)methyl)pyridin- chloride 2(1H)-ylidene]- 2,2,2-trifluoro-N′- hydroxyacetimidamide 1-518 30 mg (0.09 mmol) of 15 mg (0.18 mmol) EDC- Dichloromethane Room G 22 N-[1-((6- of 3- HCl135mg(0.18 mmol), temperature, chloropyridin-3- butynoate DMAP22mg(0.18 mmol) 21 h yl)methyl)pyridin- 2(1H)-ylidene]- 2,2,2-trifluoro-N′- hydroxyacetimidamide 1-527 30 mg (0.09 mmol) of 20 μl (0.16 mmol) 22 μl (0.16 mmol) Acetonitrile Room G 54 N-[1-((6- of phenyl of temperature, chloropyridin-3- chloroformate triethylamine 1.5 h yl)methyl)pyridin- 2(1H)-ylidene]- 2,2,2-trifluoro-N′- hydroxyacetimidamide 1-521 30 mg (0.09 mmol) of 20 mg (0.14 mmol) 40 μl (0.28 mmol) Acetonitrile Room G 46 N-[1-((6- of of temperature, chloropyridin-3- nicotinic acid triethylamine 1.5 h yl)methyl)pyridin- chloride 2(1H)-ylidene]- hydrochloride 2,2,2-trifluoro-N′- hydroxyacetimidamide 1-43  100 mg (0.30 mmol) Ethylamine (30% 90 μl (0.60 mmol) Ethanol 50° C., 1.5 h E 57 of N-[1-((6- methanol of chloropyridin-3- solution, 0.60 mmol) triethylamine, yl)methyl)pyridin- 91 mg (0.33 mmol) 2(1H)-ylidene]- of 2,2,2- silver trifluoroethanethioamide carbonate 1-536 50 mg (0.15 mmol) of 20 μl (0.17 mmol) tBuOK Acetonitrile Room H 30 N-[1-((6- of benzyl 5 mg(0.04 mmol) temperature, chloropyridin-3- isocyanate 1 h yl)methyl)pyridin- 2(1H)-ylidene]- 2,2,2-trifluoro-N′- hydroxyacetimidamide

TABLE 46 Reaction Compound Base and the temperature, Method Yield No. Raw material 1 Raw material 2 like Solvent Time (Table) (%) 1-42 150 mg (0.45 mmol) of N- Methylamine 124 mg (0.45 mmol) Methanol 50° C., 1 h E 56 [1-((6-chloropyridin-3- (40% methanol of yl)methyl)pyridin-2(1H)- solution, silver ylidene]-2,2,2- 1.36 mmol) carbonate trifluoroethanethioamide 1-500 50 mg (0.15 mmol) of N- 63 mg (0.75 mmol) 103 μl (0.75 mmol) Ethanol 50° C., 5 h F 50 [1-((6-chloropyridin-3- of O- of yl)methyl)pyridin-2(1H)- methyl triethylamine, ylidene]-2,2,2- hydroxylamine 41 mg (0.15 mmol) trifluoroethanethioamide hydrochloride of silver carbonate 1-504 50 mg (0.15 mmol) of N- 95 mg (0.75 mmol) 165 μl (1.20 mmol) Ethanol 50° C., 5 h F 19 [1-((6-chloropyridin-3- of O-t- of yl)methyl)pyridin-2(1H)- butyl triethylamine, ylidene]-2,2,2- hydroxylamine 62 mg (0.23 mmol) trifluoroethanethioamide hydrochloride of silver carbonate 1-534 40 mg (0.12 mmol) of N- 11 mg (0.13 mmol) tBuOK4mg (0.04 mmol) Acetonitrile Room H 32 [1-((6-chloropyridin-3- of n- temperature, yl)methyl)pyridin-2(1H)- propyl 1 h ylidene]-2,2,2-trifluoro- isocyanate N′-hydroxyacetimidamide 1-535 40 mg (0.12 mmol) of N- 14 mg (0.13 mmol) tBuOK4mg (0.04 mmol) Acetonitrile Room H 54 [1-((6-chloropyridin-3- of temperature, yl)methyl)pyridin-2(1H)- chloroethyl 1 h ylidene]-2,2,2-trifluoro- isocyanate N′-hydroxyacetimidamide 1-72 150 mg (0.45 mmol) of N- 74 μl (0.68 mmol) 137 mg (0.50 mmol) Ethanol 50° C., 3 h E 45 [1-((6-chloropyridin-3- of of silver yl)methyl)pyridin-2(1H)- benzylamine carbonate ylidene]-2,2,2- trifluoroethanethioamide 1-150 100 mg (0.30 mmol) of N- 56 μl (0.60 mmol) 91 mg (0.33 mmol) Ethanol 50° C., 5 h E 50 [1-((6-chloropyridin-3- of of silver yl)methyl)pyridin-2(1H)- methylthioethylamine carbonate ylidene]-2,2,2- trifluoroethanethioamide 1-67 100 mg (0.30 mmol) of N- 74 μl (1.20 mmol) 91 mg (0.33 mmol) Ethanol 50° C., 2 h E 49 [1-((6-chloropyridin-3- of 2- of silver yl)methyl)pyridin-2(1H)- aminoethanol carbonate ylidene]-2,2,2- trifluoroethanethioamide 1-515 30 mg (0.09 mmol) of N- 40 μl (0.44 mmol) 30 μl (0.22 mmol) Acetonitrile 50° C., 2 h G 67 [1-((6-chloropyridin-3- of of yl)methyl)pyridin-2(1H)- cyclopropanecarboxylic triethylamine ylidene]-2,2,2-trifluoro- acid chloride N′-hydroxyacetimidamide 1-56 100 mg (0.30 mmol) of N- 38 μl (0.60 mmol) 91 mg (0.33 mmol) Ethanol 50° C., 2 h → E 57 [1-((6-chloropyridin-3- of of silver reflux, 2 h yl)methyl)pyridin-2(1H)- propargylamine carbonate ylidene]-2,2,2- trifluoroethanethioamide 1-512 30 mg (0.09 mmol) of N- 20 μl (0.23 mmol) 34 μl (0.25 mmol) Acetonitrile Room G 32 [1-((6-chloropyridin-3- of of temperature, yl)methyl)pyridin-2(1H)- propionyl triethylamine 30 min ylidene]-2,2,2-trifluoro- chloride N′-hydroxyacetimidamide 1-514 30 mg (0.09 mmol) of N- 20 μl (0.19 mmol) 27 μl (0.20 mmol) Acetonitrile Room G 61 [1-((6-chloropyridin-3- of of temperature, yl)methyl)pyridin-2(1H)- isopropionyl triethylamine 2 h ylidene]-2,2,2-trifluoro- chloride N′-hydroxyacetimidamide 1-50 100 mg (0.30 mmol) of N- 48 μl (1.20 mmol) 91 mg (0.33 mmol) Ethanol 50° C., 1.5 h → E 44 [1-((6-chloropyridin-3- of of silver reflux, 4.5 h yl)methyl)pyridin-2(1H)- cyclopropylamine carbonate ylidene]-2,2,2- trifluoroethanethioamide

TABLE 47 Reaction Compound Base and temperature, Method Yield No. Raw material 1 Raw material 2 the like Solvent Time (Table) (%) 1-114 80 mg (0.30 mmol) of N- 48 μl (0.36 mmol) of 73 mg Ethanol 50° C., 3.5 h E 52 [1-((6-chloropyridin-3- 2- (0.33 mmol) yl)methyl)pyridin-2(1H)- phenyloxyethylamine of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-44 80 mg (0.30 mmol) of N- 60 μl (0.72 mmol) of 73 mg Ethanol 50° C., 2 h E 55 [1-((6-chloropyridin-3- n-propylamine (0.33 mmol) yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-118 100 mg (0.30 mmol) of N- 62 μl (0.60 mmol) of 91 mg Ethanol 50° C., 5 h E 70 [1-((6-chloropyridin-3- 2- (0.33 mmol) yl)methyl)pyridin-2(1H)- aminomethylpyridine of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-119 100 mg (0.30 mmol) of N- 62 μl (0.60 mmol) of 91 mg Ethanol 50° C., 5 h E 58 [1-((6-chloropyridin-3- 3- (0.33 mmol) yl)methyl)pyridin-2(1H)- aminomethylpyridine of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-47 100 mg (0.30 mmol) of N- 44 mg (0.60 mmol) of 91 mg Ethanol 50° C., 5 h E 49 [1-((6-chloropyridin-3- n-butylamine (0.33 mmol) yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-55 100 mg (0.30 mmol) of N- CH2═CHCH2NH2 34 mg 91 mg Ethanol 50° C., 2 h → E 53 [1-((6-chloropyridin-3- (0.60 mmol) (0.33 mmol) reflux, 1 h yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-122 100 mg (0.30 mmol) of N- H2NCH2-(2-thienyl) 91 mg Ethanol 50° C., 2 h → E 30 [1-((6-chloropyridin-3- 68 mg(0.60 mmol) (0.33 mmol) reflux, 1 h yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-45 100 mg (0.30 mmol) of N- 70 mg (1.20 mmol) of 91 mg Ethanol 50° C., 2 h → E 35 [1-((6-chloropyridin-3- isopropylamine (0.33 mmol) reflux, 5 h yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-124 100 mg (0.30 mmol) of N- H2NCH2-(2-furanyl) 91 mg Ethanol 50° C., 2.5 h E 56 [1-((6-chloropyridin-3- 58 mg(0.60 mmol) (0.33 mmol) yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-126 100 mg (0.30 mmol) of N- H2NCH2-(2- 91 mg Ethanol 50° C., 1 h E 43 [1-((6-chloropyridin-3- thienyldrofuranyl) (0.33 mmol) yl)methyl)pyridin-2(1H)- 61 mg(0.60 mmol) of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-64 100 mg (0.30 mmol) of N- 110 mg (1.20 mmol) 91 mg Ethanol 50° C., 1 h → E 22 [1-((6-chloropyridin-3- of aminoacetonitrile (0.33 mmol) reflux, 6 h yl)methyl)pyridin-2(1H)- hydrochloride of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-146 100 mg (0.30 mmol) of N- CH3OCH2CH2NH2 91 mg Ethanol 50° C., 5 h E 30 [1-((6-chloropyridin-3- 45 mg(0.60 mmol) (0.33 mmol) yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-52 100 mg (0.30 mmol) of N- 51 mg (0.60 mmol) of 91 mg Ethanol 50° C., 4 h E 30 [1-((6-chloropyridin-3- cyclopentylamine (0.33 mmol) yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-121 100 mg (0.30 mmol) of N- 65 mg (0.60 mmol) of 91 mg Ethanol 60° C., 4 h E 33 [1-((6-chloropyridin-3- 4-aminomethyl (0.33 mmol) yl)methyl)pyridin-2(1H)- pyridine of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate

TABLE 48 Reaction Compound Base and temperature, Method Yield No. Raw material 1 Raw material 2 the like Solvent Time (Table) (%) 1-53 100 mg (0.30 mmol) of N- 59 mg (0.60 mmol) of 91 mg Ethanol 60° C., 2 h E 28 [1-((6-chloropyridin-3- cyclohexylamine (0.33 mmol) yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate 1-76 100 mg (0.30 mmol) of N- 73 mg (0.60 mmol) of 91 mg Ethanol 60° C., 4 h E 60 [1-((6-chloropyridin-3- phenethylamine (0.33 mmol) yl)methyl)pyridin-2(1H)- of ylidene]-2,2,2- silver trifluoroethanethioamide carbonate

TABLE 49 MS or IR Compound (KBr, v, No. 1H-NMR (CDCl3, δ, ppm) cm⁻¹) 266-2   5.62 (2H, s), 7.33 (1H, d), 7.83 m/z = 323 (1H, d), 8.57 (2H, m) (M + H) 444-2   5.73 (2H, s), 7.69 (1H, s), 8.56 m/z = 329 (1H, s) (M + H) 190-2   5.39 (2H, s), 6.87 (1H, dd), m/z = 317 7.36 (1H, d), 7.91 (1H, dd), (M + H) 8.39 (1H, d), 8.49 (1H, s), 8.79 (1H, d) 201-2   5.45 (2H, s), 7.37 (1H, d), 7.65 m/z = 317 (1H, d), 7.87 (1H, dd), 7.99 (M + H) (1H, d), 8.49 (1H, d), 9.80 (1H, d) 223-2   5.69 (2H, s), 7.31 (1H, d), 7.55 m/z = 317 (1H, dd), 7.92 (1H, dd), 8.28 (M + H) (1H, dd), 8.59 (1H, d), 8.78 (1H, dd) 146-2   5.64 (2H, s), 7.14 (1H, dd), m/z = 332 7.33 (1H, d), 7.47 (1H, dd), (M + H) 7.71 (1H, dd). 7.74 (1H, dd), 8.42 (1H, d), 11.64 (1H, br s) 224-2   5.78 (2H, s), 7.57, 7.63 (1H, m/z = 323 dd × 2), 7.70 (1H, s), 8.26, 8.41 (M + H) (1H, dd × 2), 8.82, 9.04 (1H, dd × 2) 102-2   5.56 (2H, s), 7.15 (1H, m), 7.38 m/z = 341 (1H, d), 7.84 (1H, dd), 8.26 (M + H) (1H, dd), 8.48 (1H, d), 8.60 (1H, d) 212-2   5.43 (2H, s), 7.35 (1H, d), 7.87 m/z = 317 (1H, dd), 8.20 (1H, d), 8.29 (M + H) (1H, d), 8.51 (1H, d), 8.77 (1H, s) 1-20 5.48 (2H, s), 7.12 (1H, td), m/z = 332 7.34 (1H, d), 7.77 (1H, dd), (M + H) 7.96 (1H, m), 8.05 (1H, dd), 8.45 (1H, d), 8.56 (1H, d) 12-2  5.54 (2H, s), 6.96 (1H, m), 7.21 m/z = 316 (1H, d), 7.87 (1H, m), 7.97 (1H, (M + H) m), 8.34 (1H, d), 8.50 (1H, d) 213-2   5.51 (2H, s), 7.69 (1H, s), 8.25 m/z = 323 (1H, d), 8.30 (1H, d), 8.57 (1H, (M + H) s) 1-17 4.52 (2H, q), 5.44 (2H, s), 6.85 m/z = 346 (1H, td), 7.31 (1H, d), 7.57 (2H, (M + H) m), 7.79 (1H, dd), 8.14 (1H, d), 8.40 (1H, d) 1-18 1.44 (3H, d), 5.31 (1H, m), 5.42 m/z = 360 (2H, q), 6.54 (1H, td), 7.30 (1H, (M + H) d), 7.53 (2H, m). 7.79 (1H, dd), 8.10 (1H, d), 8.40 (1H, d) 1-19 5.47 (2H, s), 5.81 (1H, m), 6.69 m/z = 414 (1H, m), 7.31 (1H, d), 7.65 (1H, (M + H) m), 7.68 (1H, dd), 7.85 (1H, dd), 8.17 (1H, d), 8.40 (1H, d) 7-2  5.57 (2H, s), 6.91 (1H, m), 7.80 (1H, m), 8.10 (1H, m), 8.47 (1H, s), 8.49 (1H, d), 8.72 (1H, d) 1-13 3.22 (2H, q), 5.46 (2H, s), 6.65 m/z = 330 (1H, td), 7.31 (1H, d), 7.62 (1H, (M + H) m), 7.66 (1H, dd). 7.70 (1H, dd), 8.35 (1H, d), 8.41 (1H, d) 168-2   5.11 (2H, s), 7.40 (2H, m), 7.75 m/z = 332.0426 (1H, dd), 8.09 (1H, d), 8.15 (1H, (M + H) d), 8.46 (1H, d), 8.81 (1H, br s) 1-21 5.49 (2H, s), 6.21 (1H, t), 7.05 m/z = 314.0346 (1H, td), 7.34 (1H, d), 7.82 (1H, (M + H) dd), 7.90 (1H, m), 7.94 (1H, dd), 8.45 (1H, d), 8.49 (1H, d) 3-20 5.51 (2H, s), 6.95 (1H, d), 7.15 m/z = 316.0559 (1H, td), 7.96 (2H, m), 8.09 (1H, (M + H) d), 8.29 (1H, d), 8.52 (1H, d) 4-20 5.47 (2H, s), 7.13 (1H, m), 7.50 m/z = 375.9 (1H, m), 7.66 (1H, m), 7.97 (1H, (M + H) m), 8.07 (1H, m), 8.43 (1H, s), 8.54 (1H, m) 3-3  5.54 (2H, s), 5.92 (1H, t), 6.79 (1H, td), 6.94 (1H, dd), 7.70 (1H, m), 7.78 (1H, dd), 8.03 (1H, td), 8.30 (1H, d), 8.50 (1H, d) 4-3  5.50 (2H, s), 5.90 (1H, t), 6.79 m/z = 342 (1H, m), 7.48 (1H, d), 7.74 (3H, (M + H) m), 8.43 (1H, d), 8.50 (1H, d) 5-5  5.56 (2H, s), 6.91 (1H, m), 7.69 m/z = 384.0372 (1H, dd), 7.82 (2H, m), 8.26 (1H, (M + H) d), 8.60 (1H, d) 6-5  5.52 (2H, s), 6.93 (1H, m), 7.86 m/z = 367.0687 (2H, m). 8.61 (1H, d), 8.75 (2H, (M + H) s) 1-22 5.49 (2H, s), 7.09 (1H, td), m/z = 347.9972 7.35 (1H, d), 7.78 (1H, dd), (M + H) 7.95 (2H, m), 8.46 (1H, d), 8.55 (1H, d) 1-23 5.47 (2H, s), 7.10 (1H, td), m/z = 382.0246 7.34 (1H, d), 7.68 (1H, dd), (M + H) 7.95 (2H, m), 8.41 (1H, d), 8.55 (1H, dd) 5-20 5.49 (2H, s), 7.10 (1H, m), 7.65 m/z = 350.0188 (1H, dd), 7.96 (1H, m), 8.00 (M + H) (1H, m), 8.27 (1H, d), 8.63 (1H, d) 5-3  5.53 (2H, s), 5.90 (1H, t), 6.80 m/z = 316.0507 (1H, td), 7.76 (2H, m), 8.29 (M + H) (1H, d), 8.52 (1H, d)

TABLE 50 MS or IR Compound (KBr, v. No. 1H-NMR (CDCl3, δ, ppm) cm⁻¹) 6-3 5.45 (2H, s), 5.89 (1H, t), 6.83 m/z = 299.0532 (1H, td), 7.75 (1H, m), 7.82 (M + H) (1H, dd), 8.52 (1H, d), 8.81 (2H, s) 8-2 5.73 (2H, s), 6.90 (1H, td), 7.54 (1H, d), 7.81 (1H, td), 7.97 (1H, d), 8.22 (1H, d), 8.53 (1H, d) 5-4 5.54 (2H, s), 6.86 (1H, td), m/z = 350.0082 7.99 (3H, m). 8.30 (1H, d), 8.54 (M + H) (1H, d) 4-4 5.52 (2H, s), 6.86 (1H, td), m/z = 375.96 7.49 (1H, d), 7.77 (2H, m), 7.83 (M + H) (1H, dd), 8.45 (1H, d), 8.52 (1H, d) 6-4 5.49 (2H, s), 6.90 (1H, td), m/z = 333.0121 7.82 (1H, td), 7.87 (1H, dd), (M + H) 8.54 (1H, d), 8.81 (2H, s) 4-5 5.53 (2H, s), 6.89 (1H, td), m/z = 410 7.48 (1H, d), 7.70 (1H, dd), (M + H) 7.82 (2H, m), 8.41 (1H, d), 8.58 (1H, d)  2-20 5.57 (2H, s), 7.12 (1H, m), 7.68 m/z = 338 (1H, s), 7.97 (1H, m), 8.12 (1H, (M + H) d), 8.67 (1H, d) 10-20 5.58 (2H, s), 7.12 (1H, m), 7.70 m/z = 366 (1H, d), 7.97 (2H, m), 8.02 (1H, (M + H) d), 8.62 (1H, d), 8.77 (1H, s) 3-4 5.55 (2H, s), 6.86 (1H, td), m/z = 316 6.95 (1H, dd), 7.77 (1H, td), (M + H) 7.85 (1H, dd), 8.06 (1H, td), 8.31 (1H, d), 8.53 (1H, d) 3-5 5.56 (2H, s), 6.89 (1H, m), 6.94 m/z = 350 (1H, dd), 7.80 (2H, m), 7.97 (M + H) (1H, td), 8.27 (1H, d), 8.58 (1H. d) 11-20 1.69 (1H, m), 2.07 (1H, m), 2.84 m/z = 291 (1H, m), 3.59 (1H, dd), 3.71 (M + H) (1H, dd), 3.77 (1H, m), 3.96 (1H, m), 4.13 (1H, dd), 4.42 (1H, dd), 7.11 (1H, m), 7.92 (1H, dd), 7.98 (1H, m), 8.40 (1H, d)  1-14 5.44 (2H, s), 5.61 (1H, dd), m/z = 274 6.28 (1H, dd), 6.36 (1H, dd), (M + H) 6.52 (1H, m), 7.30 (1H, d), 7.52 (1H, m), 7.57 (1H, d), 7.73 (1H, dd), 8.28 (1H, d), 8.44 (1H, d)  1-37 1.28 (3H, t), 2.88 (2H, q), 5.41 m/z = 292 (2H, s), 6.86 (1H, t), 7.35 (1H, (M + H) d), 7.75 (3H, m), 8.10 (1H, d), 8.44 (1H, d)  1-39 1.26 (6H, d), 2.55 (1H, m), 5.51 m/z = 306 (2H, s), 6.98 (1H, m), 7.36 (1H, (M + H) d), 7.76 (1H, dd), 7.77 (2H, m), 8.08 (1H, d), 8.44 (1H, d)  1-40 0.92 (2H, m), 1.22 (2H, m), 2.40 m/z = 304 (1H, m), 5.36 (2H, s), 6.77 (1H, (M + H) td), 7.34 (1H, d), 7.66 (2H, m), 7.71 (1H, dd), 8.14 (1H, d), 8.41 (1H, d)  1-15 5.08 (2H, d), 5.40 (2H, s), 5.84 m/z = 286 (1H, t), 6.50 (1H, m), 7.30 (1H, (M + H) d), 7.50 (1H, m), 7.56 (1H, m), 7.80 (1H, dd), 8.25 (1H, d), 8.47 (1H, d)  1-35 3.18 (4H, m), 5.05 (2H, s), 6.83 m/z = 368 (1H, td), 7.05 (1H, t), 7.25 (M + H) (2H, m), 7.38 (3H, m), 7.59 (1H, dd), 7.67 (1H, d), 7.72 (1H, td), 7.99 (1H, d), 8.30 (1H, d)  1-501 1.20 (3H, t), 4.10 (2H, q), 5.22 m/z = 359 (2H, s), 6.15 (1H, td), 6.27 (M + H) (1H, d), 7.13 (1H, m), 7.27 (2H, m), 7.79 (1H, dd), 8.37 (1H, d)  1-499 5.26 (2H, s), 6.11 (1H, d), 6.31 m/z = 331 (1H, m), 7.31 (1H, m), 7.50 (1H, (M + H) d), 7.83 (1H, dd), 7.90 (1H, dd), 8.44 (1H, d), 11.0 (1H, s)  1-510 5.07 (2H, s), 5.19 (2H, s), 6.13 m/z = 421 (1H, td), 6.22 (1H, d), 7.07 (M + H) (1H, m), 7.18-7.40 (8H, m), 7.69 (1H, dd), 8.34 (1H, d)  1-511 1.99 (3H, s), 5.27 (2H, s), 6.37 m/z = 373 (2H, m), 7.31 (2H, m), 7.44 (1H, (M + H) dd), 7.76 (1H, dd), 8.37 (1H. d)  1-519 5.31 (2H, s), 6.36 (1H, t), 6.51 m/z = 435 (1H, d), 7.17 (1H, d), 7.25 (4H, (M + H) m), 7.50 (3H, m), 7.78 (1H, dd), 8.41 (1H, d)  1-523 3.84 (3H, s), 5.26 (2H, s), 6.35 m/z = 389 (1H, m), 6.40 (1H, d), 7.30 (2H, (M + H) m), 7.37 (1H, dd), 7.73 (1H, dd), 8.37 (1H, d)  1-528 3.14 (3H, s), 5.27 (2H, s), 6.44 m/z = 409 (1H, td), 6.54 (1H, dd), 7.32 (M + H) (1H, d), 7.41 (2H, m), 7.68 (1H, dd), 8.39 (1H, d)  1-531 2.45 (3H, s), 5.23 (2H, s), 6.37 m/z = 485 (1H, d), 6.42 (1H, td), 7.29 (M + H) (4H, m), 7.45 (1H, d), 7.70 (1H, dd), 7.80 (2H, d), 8.35 (1H, d)  1-507 4.54 (2H, m), 5.16 (2H, m), 5.22 m/z = 371 (2H, s), 5.91 (1H, m), 6.17 (1H, (M + H) td), 6.29 (1H, d), 7.15 (1H, m), 7.27 (2H, m), 7.79 (1H, dd), 8.37 (1H, d)

TABLE 51 MS or IR Compound (KBr, v, No. 1H-NMR (CDCl3, δ, ppm) cm⁻¹) 1-516 5.27 (2H, s), 5.76 (1H, dd), 5.91 m/z = 385 (1H, dd), 6.22 (1H, dd), 6.36 (1H, (M + H) m), 6.42 (1H, d), 7.29 (2H, m), 7.42 (1H, d), 7.76 (1H, dd), 8.37 (1H, d) 1-518 1.25 (1H, s), 1.98 (2H, s), 5.28 m/z = 397 (2H, s), 6.38 (2H, m), 7.30 (2H, m), (M + H) 7.41 (1H, d), 7.75 (1H, dd), 8.38 (1H, d) 1-527 5.28 (2H, s), 6.39 (1H, m), 6.50 m/z = 451 (1H, d), 7.13 (1H, d), 7.22-7.41 (M + H) (7H, m), 7.76 (1H, dd), 8.40 (1H, d) 1-521 5.30 (2H, s), 6.42 (1H, t), 6.52 m/z = 436 (1H, d), 7.20 (1H, d), 7.32 (2H, m), (M + H) 7.53 (1H, dd), 7.75 (1H, dd), 8.01 (1H, dd), 8.41 (1H, d), 8.54 (1H, d), 8.71 (1H, dd) 1-43 1.13(3H, t), 3.03 (2H, q), 5.15 (2H, m/z = 343 s), 6.12 (1H, m), 6.19 (1H, d), (M + H) 7.14(1H, m), 7.27 (1H, m), 7.33 (1H, d), 7.72 (1H, dd), 8.37 (1H, d) 1-536 4.48 (2H, d), 5.25 (2H, s), 6.36 m/z = 464 (1H, td), 6.41 (1H, d), 6.79 (1H, (M + H) m), 7.41 (7H, m), 7.73 (1H, dd), 8.40 (1H, d) 1-42 2.86 (3H, s), 5.16 (2H, s), 6.15 m/z = 329 (2H, m), 7.16 (1H, m), 7.26 (1H, (M + H) dd), 7.31 (1H, d), 7.73 (1H, dd), 8.38 (1H, d) 1-500 3.86 (3H, s), 5.22 (2H, s), 6.17 m/z = 345 (1H, m), 6.26 (1H, d), 7.14 (1H, m), (M + H) 7.23 (1H, dd), 7.30 (1H, d), 7.78 (1H, dd), 8.39 (1H, d) 1-504 1.23 (9H, s), 5.23 (2H, s), 6.10 m/z = 387 (1H, m), 6.22 (1H, d), 7.09 (1H, m), (M + H) 7.20 (1H, dd), 7.26 (1H, m), 7.79 (1H, dd), 8.35 (1H, d) 1-534 0.95 (3H, t), 1.61 (2H, m), 3.23 m/z = 416 (2H, t), 5.24 (2H, s), 6.32 (1H, t), (M + H) 6.39 (1H, d), 6.48 (1H, m), 7.33 (3H, m), 7.74 (1H, dd), 8.40 (1H, d) 1-535 3.65 (4H, m), 5.25 (2H, s), 6.36 m/z = 436 (1H, t), 6.41 (1H, d), 6.82 (1H, (M + H) m), 7.36 (3H, m), 7.74 (1H, dd), 8.41 (1H, d) 1-72 4.22 (2H, s), 5.13 (2H, s), 6.14 m/z = 405 (1H, m), 6.21 (1H, d), 7.13 (1H, (M + H) m), 7.26 (7H, m), 7.68 (1H, dd), 8.36 (1H, d) 1-150 2.08 (3H, s), 2.70 (2H, t), 3.22 m/z = 389 (2H, t), 5.15 (2H, s), 6.16 (1H, (M + H) t), 6.22 (1H, d), 7.17 (1H, m), 7.29 (1H, d), 7.33 (1H, d), 7.70 (1H, dd), 8.38 (1H, d) 1-67 3.13 (2H, m), 3.73 (2H, t), 5.15 m/z = 359 (2H, s), 6.18 (2H, m), 7.17 (1H, (M + H) m), 7.33 (2H, m), 7.71 (1H, dd), 8.37 (1H, d) 1-515 0.82 (2H, m), 0.93 (2H, m), 1.40 m/z = 399 (1H, m), 5.27 (2H, s), 6.35 (1H, (M + H) m), 6.42 (1H, d), 7.31 (2H, m), 7.41 (1H, d), 7.77 (1H, dd), 8.38 (1H, d) 1-56 2.13 (1H, t), 3.85 (2H, d), 5.18 m/z = 353 (2H, s), 6.21 (1H, t), 6.25 (1H, (M + H) d), 7.18 (1H, m), 7.29 (1H, d), 7.33 (1H, d), 7.70 (1H, dd), 8.38 (1H, d) 1-512 1.02 (3H, t), 2.23 (2H, q), 5.26 m/z = 387 (2H, s), 6.34 (1H, m), 6.39 (1H, (M + H) m), 7.29 (2H, m), 7.40 (1H, d), 7.75 (1H, dd), 8.37 (1H, d) 1-514 0.97 (6H, s), 2.37 (1H, m), 5.26 m/z = 399 (2H, s), 6.35 (1H, m), 6.40 (1H, (M + H) d), 7.27 (2H, m), 7.42 (1H, dd), 7.77 (1H, dd), 8.38 (1H, d) 1-50 0.74 (2H, m), 0.85 (2H, m), 2.51 m/z = 355 (1H, m), 5.18 (2H, s), 6.12 (1H, (M + H) m), 6.30 (1H, d), 7.15 (1H, m), 7.27 (1H, m), 7.31 (1H, d), 7.79 (1H, dd), 8.39 (1H, d) 1-114 3.44 (2H, td), 4.18 (2H, t), m/z = 435 5.14 (2H, s), 6.15 (1H, td), (M + H) 6.26 (1H, d), 6.86 (2H, d), 6.92 (1H, m), 7.16 (1H, m), 7.28 (4H, m), 7.71 (1H, dd), 8.38 (1H, d) 1-44 0.83 (3H, t), 1.55 (2H, m), 2.91 m/z = 357 (2H, m), 5.14 (2H, s), 6.12 (1H, (M + H) td), 6.18 (1H, d), 7.13 (1H, m), 7.30 (2H, m), 7.71 (1H, dd), 8.36 (1H, d) 1-118 4.41 (2H, s), 5.15 (2H, s), 6.18 m/z = 406 (1H, t), 6.24 (1H, d), 7.14 (2H, (M + H) m), 7.26 (2H, m), 7.54 (1H, d), 7.68 (1H, dd), 7.71 (1H, dd), 8.38 (1H, d), 8.47 (1H, d) 1-119 4.22 (2H, s), 5.16 (2H, s), 6.20 m/z = 406 (2H, m), 7.15-7.30 (3H, m), 7.34 (M + H) (1H, dd), 7.61 (1H, d), 7.79 (1H, dd), 8.37 (1H, d), 8.42 (1H, d), 8.46 (1H, d)

TABLE 52 MS or IR Compound (KBr, v, No. 1H-NMR (CDCl3, δ, ppm) cm⁻¹) 1-47 0.85 (3H, t), 1.25 (2H, m), m/z = 371 1.53 (2H, m), 2.96 (2H, m), 5.14 (2H, (M + H) s), 6.10 (1H, m), 6.17 (1H, d), 6.99 (1H, m), 7.27 (2H, m), 7.70 (1H, dd), 8.36 (1H, d) 1-55 3.65 (2H, m), 5.04 (2H, m), m/z = 355 5.15 (2H, s), 5.90 (1H, m), 6.13 (1H, (M + H) m), 6.20 (1H, d), 7.13 (1H, m), 7.28 (2H, m), 7.71 (1H, dd), 8.36 (1H, d)  1-122 4.41 (2H, s), 5.17 (2H, s), m/z = 411 6.17 (2H, m), 6.82 (1H, m), 6.91 (1H, (M + H) m), 7.16 (2H, m), 7.30 (2H, m), 7.70 (1H, dd), 8.38 (1H, d) 1-45 1.02 (6H, d), 3.34 (1H, m), m/z = 357 5.13 (2H, s), 6.10 (1H, m), 6.24 (1H, (M + H) d), 7.11 (1H, m), 7.26 (1H, m), 7.31 (1H, d), 7.68 (1H, dd), 8.35 (1H, d)  1-124 4.20 (2H, s), 5.17 (2H, s), m/z = 395 6.13-6.29 (4H, m), 7.17 (1H, m), (M + H) 7.30 (3H, m), 7.71 (1H, dd), 8.38 (1H, d)  1-126 1.49 (1H, m), 1.84 (2H, m), m/z = 399 1.99 (1H, m), 2.98 (1H, ddd), (M + H) 3.14 (1H, ddd), 3.73 (2H, m), 4.09 (1H, m), 5.13 (2H, m), 6.13 (1H, m), 6.20 (1H, d), 7.14 (1H, m), 7.30 (2H, m), 7.70 (1H, dd), 8.37 (1H, d) 1-64 4.01 (2H, s), 5.24 (2H, s), m/z = 354 6.34 (2H, m), 7.34 (2H, m), 7.41 (1H, (M + H) dd), 7.66 (1H, dd), 8.36 (1H, d)  1-146 3.21 (2H, m), 3.34 (2H, s), m/z = 373 3.57 (2H, t), 5.14 (2H, s), 6.15 (1H, (M + H) m), 6.21 (1H, m), 7.15 (1H, m), 7.30 (2H, m), 7.72 (1H, dd), 8.37 (1H, d) 1-52 1.40-1.77 (8H, m), 3.48 (1H, m), m/z = 383 5.12 (2H, s), 6.09 (1H, m), (M + H) 6.23 (1H, d), 7.12 (1H, m), 7.24 (1H, m), 7.31 (1H, d), 7.69 (1H, dd), 8.35 (1H, d)  1-121 4.18 (2H, s), 5.14 (2H, s), m/z = 406 6.20 (2H, m), 7.19 (3H, m), 7.26 (1H, (M + H) m), 7.35 (1H, dd), 7.75 (1H, dd), 8.36 (1H, d), 8.51 (2H, m) 1-53 0.98-1.72 (10H, m), 2.91 (1H, m/z = 397 m), 5.11 (2H, s), 6.11 (1H, td), (M + H) 6.24 (1H, d), 7.11 (1H, m), 7.29 (3H, m), 7.66 (1H, dd), 8.34 (1H, d) 1-76 2.90 (2H, t), 3.24 (2H, td), m/z = 419 5.07 (2H, s), 6.01 (1H, d), (M + H) 6.09 (1H, td), 7.02-7.30 (8H, m), 7.61 (1H, dd), 8.34 (1H, d) 267-2   4.34 (1H, d), 4.62 (1H, d), 1730, 6.40 (1H, d), 7.20 (1H, d), 7.51 (2H, 1689, m), 7.59 (1H, dd), 7.63 (2H, m), 1556, 7.82 (1H, d), 8.23 (1H, d) 1467, 1440, 1418 253-2   5.31 (2H, s), 7.28 (2H, m), 1644, 7.50 (1H, d), 7.72 (3H, m), 7.85 (1H, 1557, m), 8.25 (1H, d), 8.45 (1H, d) 1508, 1483 251-2   5.20 (2H, s), 7.26 (2H, m), 3065, 7.63 (2H, m), 7.85 (2H, m), 8.02 (1H, 1696, d), 8.23 (2H, m) 1463, 1403 13-2  5.76 (2H, s), 6.91 (1H, m), 3060, 7.46 (1H, m), 7.60 (1H, m), 7.70 (1H, 2226, d), 7.80 (2H, m), 8.12 (1H, d), 1641, 8.53 (1H, d) 1556, 1509 1-1  5.49 (2H, s), 6.67 (1H, m), — 7.30 (1H, m), 7.60 (1H, m), 7.72 (2H, m), 7.81 (1H, dd), 8.42 (1H, d), 9.06 (1H, s) 1-41 5.64 (2H, s), 7.50 (2H, m), m/z = 315.16 7.70 (1H, d), 7.78 (1H, dd), (M + H) 8.27 (1H, m), 8.37 (1H, d), 8.78 (1H, d) (methanol-d4)

TABLE 53 MS or IR Compound (KBr, v, No. 1H-NMR (CDCl3, δ, ppm) cm⁻¹) 2-2  2.47 (2H, m), 4.17 (2H, t), m/z = 322 5.07 (1H, d), 5.15 (1H, dd), 5.39 (2H, (M + H) s), 5.85 (1H, m), 6.43 (1H, td), 7.30 (1H, d), 7.44 (2H, m), 7.75 (1H, dd), 8.08 (1H, d), 8.40 (1H, d) 1-647 2.47 (2H, m), 4.17 (2H, t), m/z = 5.07 (1H, d), 5.15 (1H, dd), 5.39 (2H, 318.1013 s), 5.85 (1H, m), 6.43 (1H, td), (M + H) 7.30 (1H, d), 7.44 (2H, m), 7.75 (1H, dd), 8.08 (1H, d), 8.40 (1H, d) 1-670 3.35 (2H, tdd), 5.17 (2H, s), m/z = 379 6.02 (1H, tt), 6.23 (2H, m), 7.22 (1H, (M + H) m), 7.33 (2H, m), 7.69 (1H, dd), 8.37 (1H, d) 157-2   5.51 (2H, s), 6.63 (1H, dd), m/z = 332 7.42 (1H, d), 7.77 (1H, d), 7.84 (1H, (M + H) dd), 8.26 (1H, d), 8.45 (1H, d) 1-10  1.61 (1H, m), 2.29 (2H, m), m/z = 324 4.73 (2H, s), 7.26 (1H, m), 7.31 (1H, m), (M + H) 7.69 (1H, m), 7.79 (1H, m), 8.23 (1H, d), 8.40 (1H, d), 8.57 (1H, d) 580-2   5.47 (2H, s), 6.89 (1H, m), m/z = 332 7.47 (2H, m), 7.82 (2H, m), 8.41 (1H, s), (M + H) 8.56 (1H, d) 1-671 0.87 (3H, t), 1.28 (10H, m), m/z = 427 1.55 (2H, m), 2.96 (2H, t), 5.14 (2H, s), (M + H) 6.13 (1H, t), 6.18 (1H, d), 7.13 (1H, m), 7.30 (2H, m), 7.71 (1H, dd), 8.37 (1H, d) 1-658 0.87 (3H, t), 1.25 (26H, m), m/z = 539 1.55 (2H, m), 2.96 (2H, t), 5.14 (2H, s), (M + H) 6.11 (1H, t), 6.17 (1H, d), 7.13 (1H, m), 7.30 (2H, m), 7.70 (1H, dd), 8.36 (1H, d) 1-659 0.87 (3H, t), 1.26 (18H, m), m/z = 483 1.53 (2H, m), 2.95 (2H, t), 5.14 (2H, s), (M + H) 6.12 (1H, t), 6.18 (1H, d), 7.13 (1H, m), 7.31 (2H, m), 7.71 (1H, dd), 8.36 (1H, d) 1-660 0.74 (3H, t), 0.97 (3H, d), m/z = 371 1.42 (2H, m), 3.08 (1H, m), 5.12 (2H, (M + H) dd), 6.09 (1H, t), 6.23 (1H, d), 7.11 (1H, m), 7.24 (1H, m), 7.30 (1H, d), 7.67 (1H, dd), 8.35 (1H, d) 1-681 0.77, 0.90 (6H, t × 2), 1.40 (4H, m/z = 385 m), 2.97 (1H, m), 5.11 (2H, s), (M + H) 6.10 (1H, t), 6.25 (1H, d), 7.11 (1H, m), 7.24 (1H, d), 7.32 (1H, d), 7.66 (1H, dd), 8.34 (1H, d) 1-686 0.81, 0.91 (6H, t × 2), m/z = 413 1.02-1.45 (8H, m), 3.19 (1H, m), 5.12 (2H, (M + H) s), 6.10 (1H, t), 6.25 (1H, d), 7.11 (1H, m), 7.22 (1H, d), 7.30 (1H, d), 7.64 (1H, dd), 8.33 (1H, d) 1-661 0.81 (3H, t), 0.97 (3H, d), m/z = 385 0.90-1.50 (4H, m), 3.19 (1H, m), (M + H) 5.07 (1H, d), 5.15 (1H, d), 6.09 (1H, t), 6.24 (1H, d), 7.11 (1H, m), 7.27 (2H, m), 7.66 (1H, dd), 8.34 (1H, d) 1-662 0.75 (3H, d), 0.80 (3H, d), m/z = 385 0.94 (3H, d), 1.61 (1H, m), 2.86 (1H, (M + H) m), 5.11 (2H, s), 6.09 (1H, t), 6.23 (1H, d), 7.11 (1H, t), 7.25 (1H, d), 7.30 (1H, d), 7.66 (1H, dd), 8.34 (1H, d) 1-663 1.35 (3H, d), 4.33 (1H, q), m/z = 419 5.05 (1H, d), 5.11 (1H, d), 6.00 (1H, (M + H) d), 6.08 (1H, t), 6.96 (1H, m), 7.15-7.26 (7H, m), 7.63 (1H, dd), 8.33 (1H, d) 1-664 1.55-1.75 (3H, m), 1.95 (1H, m), m/z = 445 2.70-2.88 (2H, m), 4.36 (1H, t), (M + H) 5.05 (1H, d), 5.20 (1H, d), 6.13 (1H, t), 6.38 (1H, d), 6.96 (1H, m), 7.02-7.20 (5H, m), 7.28 (1H, d), 7.62 (1H, dd), 8.3 (1H, d) 1-665 1.57 (3H, d), 4.78 (1H, d), m/z = 469 4.91 (1H, d), 5.18 (1H, q), 5.80 (1H, (M + H) d), 5.93 (1H, t), 6.72 (1H, m), 7.05 (1H, d), 7.14 (1H, d), 7.38 (3H, m), 7.54 (1H, dd), 7.62 (1H, d), 7.66 (1H, d), 7.80 (1H, d), 7.84 (1H, d), 8.28 (1H, d) 1-666 0.74 (3H, t), 1.75 (2H, m), m/z = 433 4.03 (1H, t), 5.06 (2H, dd), (M + H) 5.85 (1H, d), 6.05 (1H, m), 6.86 (1H, m), 7.10-7.28 (7H, m), 7.63 (1H, dd), 8.33 (1H, d) 1-667 1.34 (3H, d), 4.45 (1H, q), m/z = 409 5.11 (1H, d), 5.16 (1H, d), 6.07 (1H, (M + H) m), 6.14 (1H, td), 6.26 (2H, m), 7.11 (1H, m), 7.28 (3H, m), 7.67 (1H, dd), 8.36 (1H, d) 1-676 5.06 (2H, s), 5.37 (1H, s), m/z = 481 5.38 (1H, d), 6.07 (1H, t), 6.85 (1H, (M + H) t), 7.10-7.28 (12H, m), 7.61 (1H, d), 8.33 (1H, s) 1-668 0.79 (9H, s), 0.85 (3H, d), m/z = 399 2.89 (1H, q), 5.11 (2H, s), 6.08 (1H, (M + H) t), 6.23 (1H, d), 7.10 (1H, t), 7.23 (1H, d), 7.30 (1H, d), 7.65 (1H, d), 8.34 (1H, s)

TABLE 54 MS or IR Compound (KBr, v, No. 1H-NMR (CDCl3, δ, ppm) cm⁻¹) 47-2   5.68 (2H, d), 6.57 (1H, m), m/z = 334 7.34 (1H, d), 7.80 (1H, m), 7.97 (1H, (M + H) dd), 8.39 (1H, d), 8.57 (1H, s) 91-2   5.92 (2H, s), 6.95 (1H, d), m/z = 350 7.30 (1H, d), 7.69 (1H, m), 7.86 (1H, (M + H) dd), 8..49 (1H, dd), 8.53 (1H, d) 478-2   2.59 (3H, s), 5.77 (2H, s), m/z = 330 6.75 (1H, d), 7.31 (1H, d), 7.63 (1H, (M + H) dd), 7.72 (1H, m), 8.33 (1H, d), 8.45 (1H, d) 479-2   2.73 (3H, s), 5.71 (2H, s), m/z = 336 6.73 (1H, d), 7.63 (1H, s), 7.69 (1H, (M + H) t), 8.44 (1H, d) 1-51  1.60 (2H, m), 1.73 (1H, m), m/z = 369 2.03 (4H, m), 3.75 (1H, m), 5.12 (2H, (M + H) s), 6.12 (1H, t), 6.16 (1H, d), 7.10 (1H, m), 7.25 (1H, d), 7.32 (1H, d), 7.71 (1H, dd), 8.37 (1H, d) 566-2   4.09 (3H, s), 5.71 (2H, s), m/z = 346 6.25 (1H, d), 7.29 (1H, d), 7.74 (1H, (M + H) t), 7.97 (1H, dd), 8.17 (1H, d), 8.50 (1H, d) 488-2   1.77 (1H, m), 2.11 (1H, m), m/z = 289 2.62 (3H, s), 2.98 (1H, m), 3.53 (1H, (M + H) dd), 3.67 (1H, dd), 3.78 (1H, m), 3.98 (1H, m), 4.22 (1H, m), 4.65 (1H, m), 6.73 (1H, d), 7.66 (1H, t), 8.32 (1H, d) 511-2   5.58 (2H, s), 7.38 (1H, d), m/z = 361 7.86 (1H, dd), 8.40 (1H, dd), (M + H) 8.47 (1H, d), 8.55 (1H, d), 8.93 (1H, d) 1-669 1.42 (3H, d), 4.65 (1H, q), m/z = 425 5.12 (2H, s), 6.13 (2H, m), 6.75 (1H, (M + H) d), 6.88 (1H, dd), 7.07 (1H, m), 7.11 (1H, d), 7.26 (2H, m), 7.65 (1H, dd), 8.35 (1H, d) 179-2   5.30 (2H, s), 6.43 (1H, dd), m/z = 332 6.66 (1H, dd), 7.40 (1H, d), (M + H) 7.60 (2H, m), 8.20 (1H, d) 555-2   3.87 (3H, s), 5.60 (2H, s), m/z = 346 7.51 (1H, d), 7.88 (1H, dd), (M + H) 7.93 (1H, dd), 8.34 (1H, d), 8.49 (1H, d), 8.56 (1H, d) (DMSO-d6) 577-2   5.65 (2H, s), 6.87 (1H, td), m/z = 349 7.30 (1H, d), 7.81 (1H, m), (M + H) 8.08 (1H, dd), 8.13 (1H, d), 8.54 (1H, d) 544-2   3.93 (3H, s), 5.45 (2H, s), m/z = 346 6.49 (1H, dd), 7.31 (1H, d), (M + H) 7.66 (1H, d), 7.83 (1H, dd), 8.13 (1H, d), 8.42 (1H, d) 168-2   5.62 (2H, s), 7.43 (1H, d), m/z = 332 7.64 (1H, dd), 7.88 (1H, dd), (M + H) 7.94 (1H, d), 8.26 (1H, d), 8.49 (1H, d) 1-644 4.18 (2H, s), 4.68 (2H, s), m/z = 368 5.36 (2H, s), 6.55 (1H, m), (M + H) 7.16 (1H, d), 7.29 (1H, d), 7.35 (2H, m), 7.40 (2H, m), 7.52 (2H, m), 7.75 (1H, dd), 8.28 (1H, d), 8.40 (1H, d) 578-644  4.19 (2H, s), 4.69 (2H, s), m/z = 334 5.42 (2H, s), 6.52 (1H, m), (M + H) 7.20 (1H, m), 7.30 (1H, m), 7.32 (2H, m), 7.40 (2H, m), 7.55 (2H, m), 7.72 (1H, dd), 8.30 (1H, dd), 8.52 (1H, dd), 8.62 (1H, d) 1-703 5.20 (1H, d), 5.45 (1H, d), 1715, 1636, 6.55 (1H, m) 7.34 (1H, m), 1552, 1505, 7.50 (1H, m), 7.60 (1H, m), 1457, 1174, 7.79 (1H, dd), 8.39 (1H, d) 1144 1-707 5.43 (2H, s), 6.93 (1H, m), (EI-HRMS) 7.36 (1H, d), 7.77-7.85 (3H, m/z = 351.0084 m), 7.95 (1H, dd), 8.39 (1H, (M+) d) 1-706 1.20 (6H, m), 2.67 (4H, m), m/z = 298 5.22 (2H, s), 6.52 (1H, m),. (M + H) 7.31 (1H, m), 7.51 (1H, m), 7.60 (1H, dd), 7.73 (1H, m), 7.84 (1H, d), 8.41 (1H, d) 1-692 1.11 (3H, t), 1.20 (3H, t), m/z = 356 3.76 (2H, m), 3.92 (2H, m), 6.58 (1H, (M + H) m), 7.26 (1H, d)., 7.53 (2H, m), 7.74 (1H, dd), 8.12 (1H, d), 8.40 (1H, d) (DMSO-d6) 1-700 1.20 (6H, m), 2.67 (4H, m), m/z = 404 5.22 (2H, s), 6.52 (1H, m),. 7.31 (1H, (M + H) m), 7.51 (1H, m), 7.60 (1H, dd), 7.73 (1H, m), 7.84 (1H, d), 8.41 (1H, d) 1-701 0.95 (6H, m), 1.56 (4H, m), m/z = 432 2.62 (4H, m), 5.18 (2H, s), 6.52 (1H, (M + H) m), 7.34 (1H, m), 7.49 (1H, m), 7.59 (1H, m), 7.77 (1H, dd), 7.84 (1H, d), 8.42 (1H, d) 1-702 1.13-1.46 (m, 12H), 3.20 (m, 2H), m/z = 432 5.27 (s, 2H), 6.51 (m, 1H), (M + H) 7.31 (m, 1H), 7.52 (m, 1H), 7.63 (m, 1H), 7.78 (m, 2H), 8.43 (d, 1H) 1-646 1.31 (6H, d), 4.95 (1H, sep), 1646, 5.40 (2H, s), 6.40 (1H, m), 1620, 7.28 (1H, d), 7.40 (2H, m), 7.73 (1H, 1548, dd) 8.05 (1H, m), 8.40 (1H, d) 1504, 1453, 1-645 5.18 (2H, s), 5.37 (2H, s), 1655, 6.43 (1H, m), 7.25-7.36 (4H, m), 1518, 7.41-7.46 (4H, m), 7.72 (1H, 1455, dd), 8.12 (1H, m), 8.38 (1H, d) 1399, 1235 1-643 5.52 (2H, s), 6.78 (1H, m), 1633, 7.31 (1H, d), 7.68-7.75 (3H, m), 1601, 8.39 (1H, m), 8.56 (1H, s) 1541, 1502, 1482, 1453, 1384 2-643 5.51 (2H, s), 6.80 (1H, m), 1632, 7.60 (1H, s), 7.75 (2H, m), 8.57 (1H, 1597, m) 1541, 1506, 1483, 1455, 1388

Further, the synthetic methods in the Table are described as follows.

A: the same method as in Synthetic Example 1

B: the same method as in Synthetic Example 2

C: the same method as in Synthetic Example 3

D: the same method as in Synthetic Example 4

E: the same method as in Synthetic Example 5

F: the same method as in Synthetic Example 6

G: the same method as in Synthetic Examples 7 and 8

H: the same method as in Synthetic Example 9

Preparation Example Preparation Example

Preparation Example 1 [Wettable powder] Compound P212 10% by weight Imidacloprid 20% by weight Clay 50% by weight White carbon  2% by weight Diatomaceous earth 13% by weight Calcium ligninsulfonate  4% by weight Sodium lauryl sulfate  1% by weight

The ingredients were homogeneously mixed and ground to obtain wettable powder.

Preparation Example 2 [Water dispersible granule] Compound P212 10% by weight Imidacloprid 20% by weight Clay 60% by weight Dextrin  5% by weight Alkyl maleate copolymer  4% by weight Sodium lauryl sulfate  1% by weight

The ingredients were homogeneously ground and mixed, water was added thereto to knead the ingredients thoroughly and then the mixture was granulated and dried to obtain water dispersible granules.

Preparation Example 3 [Flowables] Compound 1-20 5% by weight Imidacloprid 20% by weight POE polystyrylphenyl ether sulfate 5% by weight Propylene glycol 6% by weight Bentonite 1% by weight 1% xanthan-gum aqueous solution 3% by weight PRONALEX-300 (TOHO Chemical 0.05% by weight Industry Co., Ltd.) ADDAC827 (KI Chemical Industry Co., 0.02% by weight Ltd.) Water added to 100% by weight

All the ingredients except for the 1% xanthan-gum aqueous solution and a suitable amount of water were premixed together from the blending, and the mixture was then ground by a wet grinder. Thereafter, the 1% xanthan-gum aqueous solution and the remaining water were added thereto to obtain 100% by weight of flowables.

Preparation Example 4 [Emulsifiable concentrate] Compound P212  2% by weight Imidacloprid 13% by weight N,N-dimethylformamide 20% by weight Solvesso 150 (Exxon Mobil Corporation) 55% by weight Polyoxyethylene alkyl aryl ether 10% by weight

The ingredients were homogeneously mixed and dissolved to obtain an emulsifiable concentrate.

Preparation Example 5 [Dust] Compound P212 0.5% by weight  Imidacloprid 1.5% by weight  Clay 60% by weight Talc 37% by weight Calcium stearate  1% by weight

The ingredients were homogeneously mixed to obtain dust.

Preparation Example 6 [DL Dust] Compound P212 1% by weight Tebufloquin 1% by weight Ethofenprox 1% by weight DL clay 94.5% by weight   White carbon 2% by weight Light liquid paraffin 0.5% by weight  

The ingredients were homogeneously mixed to obtain dust.

Preparation Example 7 [Microgranule fine] Compound P212 1% by weight Imidacloprid 1% by weight Carrier 94% by weight  White carbon 2% by weight Hisol SAS-296 2% by weight

The ingredients were homogeneously mixed to obtain dust.

Preparation Example 8 [Granules] Compound 1-20  2% by weight Chlorantraniliprole  1% by weight Bentonite 39% by weight Talc 10% by weight Clay 46% by weight Calcium ligninsulfonate  2% by weight

The ingredients were homogeneously ground and mixed, water was added thereto to knead the ingredients thoroughly, and then the mixture was granulated and dried to obtain granules.

Preparation Example 9 [Microcapsules] Compound 1-20 2% by weight Imidacloprid 3% by weight Urethane resin 25% by weight  Emulsifier/Dispersant 5% by weight Antiseptic 0.2% by weight   Water 64.8% by weight  

Microcapsules were obtained by forming a urethane resin coating on the surface of particles of the compound represented by Formula (I) and imidacloprid particles using the ingredients by interfacial polymerization.

Preparation Example 10 [Granules] Compound P212 2% by weight Probenazole 24% by weight  Sodium lauryl sulfate 1% by weight Bentonite 2% by weight Calcium stearate 1% by weight PVA 2% by weight Clay 68% by weight 

The ingredients were homogeneously ground and mixed, water was added thereto to knead the ingredients thoroughly, and then the mixture was granulated and dried to obtain granules.

Preparation Example 11 [Granules] Compound P212  2% by weight Chlorantraniliprole  1% by weight Probenazole 24% by weight Bentonite 40% by weight Talc 10% by weight Clay 21% by weight Calcium ligninsulfonate  2% by weight

The ingredients were homogeneously ground and mixed, water was added thereto to knead the ingredients thoroughly, and then the mixture was granulated and dried to obtain granules.

Preparation Example 12 [Liquid drops] Compound 1-20 10% by weight Fipronil  1% by weight Benzyl alcohol 73.9% by weight   Propylene carbonate 15% by weight BHT 0.1% by weight 

The ingredients were homogeneously stirred and dissolved to obtain liquid drops.

Preparation Example 13 [Liquid drops] Compound P212 48% by weight Fipronil 2% by weight Ethanol 50% by weight

The ingredients were homogeneously mixed to obtain liquid drops.

Preparation Example 14 [Emulsifiable concentrate] Compound 1-20 5% by weight Etoxazole 5% by weight Xylene 35% by weight Dimethyl sulfoxide 35% by weight

The ingredients were dissolved, and 14% by weight of polyoxyethylene styryl phenyl ether and 6% calcium dodecylbenzenesulfonate were added thereto, and the mixture was thoroughly stirred and mixed to obtain a 10% emulsifiable concentrate.

Preparation Example 15 [Liquid drops] Compound P212 10% by weight Etoxazole 5% by weight Glycol (glycol mono alkyl ether) 85% by weight BHT or BHA appropriate amount

An appropriate amount of sorbitan monooleate or sorbitan monolaurate, caprylic acid monoglyceride or isostearic acid monoglyceride, or propylene glycol monocaprylate was added to the ingredients, and alcohol or propylene carbonate, N-methyl-2-pyrrolidone or water was added thereto to obtain liquid drops as 100% by weight.

Reference Test Example Foliar Treatment Test of Single Agent Reference Test Example 1 Pest Control Test of Plutella Xylostella

A leaf disk having a diameter of 5.0 cm was cut out from a cabbage in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 2 Pest Control Test of Spodoptera litura

A leaf disk having a diameter of 5.0 cm was cut out from a cabbage in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After an air drying process, third instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 500 ppm.

Reference Test Example 3 Pest Control Test of Aphis gossypii

A leaf disk having a diameter of 2.0 cm was cut out from a cucumber in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After an air drying process, first instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 4 Pest Control Test of Laodelphax Striatella

A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 5 Pest Control Test of Nilaparvata lugens

A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Six days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 6 Pest Control Test of Sogatella furcifera

A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Four days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 7 Pest Control Test of Nephotettix cincticeps

A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Four days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compound P212 exhibited insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 8 Pest Control Test of Trialeurodes Vaporariorum

Adult greenhouse whiteflies were released to a cucumber in pot culture and allowed to lay eggs overnight. One day after the onset of egg laying, the adults were removed and the eggs were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the completion of egg laying, a leaf disk having a diameter of 2.0 cm was cut out from the cucumber, it was confirmed that the eggs had been laid, and then a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After the spraying, the leaf disk was left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Fourteen days after the spraying, larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={(number of eggs laid−number of survived larvae)/number of eggs laid)}×100

As a result, compound P212 exhibited high insecticidal activity having a mortality of 80% or higher by a foliar treatment at 100 ppm.

Reference Test Example 9 Pest Control Test of Frankliniella occidentalis

A leaf disk having a diameter of 2.8 cm was cut out from a kidney bean in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to the leaf disk. After an air drying process, first instar larvae were released to the leaf disk. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidal activity having a mortality of 80% or higher by a foliage treatment at 500 ppm.

Reference Test Example 10 Pest Control Test of Trigonotylus Caelestialium

Wheat seedling leaves and stems four days after the dissemination of seedlings were dipped for 30 seconds in a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available). After an air drying process, the wheat seedling leaves and stems were placed into a glass tube, and two second instar larvae of Trigonotylus coelestialium were released to the same glass tube. After the larvae were released, the tube was lidded to leave the larvae to stand in a thermostatic chamber at 25° C. In order to supply water to the wheat during the test, water was given to the wheat from the bottom of the glass tube. Three days after the treatment, the larvae were observed for survival or death, and the death rate of larvae was calculated by the following equation. Test in triplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited insecticidal activity having a mortality of 80% or higher by a dipping treatment of the drug solution at 50 ppm.

Reference Test Example 11 Pest Control Test of Plautia Crossota Stali

A drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed to a young fruit of apple collected outdoors. After an air drying process, the young fruit was placed into a plastic cup, and two adults of Plautia crossota stali were released thereto. Six days after the release, the adults were observed for survival or death, the Mortality of adults was calculated by the following equation.

Mortality of adults (%)={number of dead adults/(number of survived adults+number of dead adults)}×100

As a result, compound P212 exhibited insecticidal activity having a mortality of 60% or higher by a foliar treatment at 50 ppm.

Reference Test Example 12 Pest Control Test of Oulema oryzae

1 μL (/head) of a drug solution of the compound of Formula (I) prepared at a predetermined concentration with acetone was topically applied and treated to the back of adults collected outdoors by a micro syringe. After the drug treatment, the adults were transferred to rice seedlings and left to stand in a thermostatic chamber at 25° C. so as to obtain 5 heads per stem. Forty eight hours after the treatment, the adults were observed for survival or death, and the mortality of adults was calculated by the following equation. Test in duplicate.

Mortality of adults (%)={number of dead adults/(number of survived adults+number of dead adults)}×100

As a result, compound P212 exhibited high insecticidal activity having a mortality of 80% or higher in a throughput of 0.5 μg/head.

Reference Test Example 13 Pest Control Test of Musca domestica

The backs of female adults raised indoors were treated with 1 μL (/head) of a drug solution of the compound of Formula (I) prepared at a predetermined concentration with acetone. After the drug treatment, the adults were transferred to a plastic cup and left to stand in a thermostatic chamber at 25° C. so as to obtain 5 heads per cup. Twenty four hours after the treatment, the agony situation of the adults was observed, and the rate of agonized adults was calculated by the following equation. Test in duplicate.

Mortality of adults (%)={number of dead adults/(number of survived adults+dead adults)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidal activity having a mortality of 80% or higher in a throughput of 2 μg/head.

Soil Drench Test of Single Agent Reference Test Example 14 Pest Control Test of Laodelphax Striatella

A rice seedling in pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 10% acetone water. Three days after the treatment, ten second instar larvae of Laodelphax striatella were each released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidal activity having a mortality of 80% or higher in a throughput of 0.05 mg/seedling.

Reference Test Example 15 Pest Control Test of Sogatella furcifera

A rice seedling in pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, which had been prepared so as to be a 10% acetone water. Three days after the treatment, ten second instar larvae of Sogatella furcifera were each released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidal activity having a mortality of 80% or higher in a throughput of 0.05 mg/seedling.

Reference Test Example 16 Pest Control Test of Nilaparvata lugens

A rice seedling in pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I), which had been prepared so as to be a 10% acetone water. Three days after the treatment, ten second instar larvae of Nilaparvata lugens were each released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-20 exhibited high insecticidal activity having a death rate of 80% or higher in a throughput of 0.05 mg/seedling.

Reference Test Example 17 Pest Control Test of Lissorhoptrus oryzophilus

A rice seedling in pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I), which had been prepared so as to be a 10% acetone water. Two days after the treatment, five adults of Lissorhoptrus oryzophilus were each released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compound P212 exhibited high insecticidal activity having a mortality of 80% or higher in a throughput of 0.1 mg/seedling.

Reference Test Example 18 Pest Control Test of Laodelphax Striatella

Wheat seedling roots forty eight hours after the dissemination of seeds were treated with a drug solution of the compound of the present invention at a predetermined concentration, which had been prepared so as to be a 10% acetone water. The drug was absorbed from the roots for 72 hours, and then ten second instar larvae of Laodelphax striatella were each released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Four days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

As a result, compounds P212 and 1-204 exhibited insecticidal activity having a mortality of 80% or higher in a throughput of 20 μg/seedling.

The results of Reference Test Examples 1, 3 and 18 are shown in the following Table.

TABLE 55 Plutella Laodelphax xylostella Aphisgossypii striatella Reference (Reference (Reference (Reference Example Test Test Test Compound Example Example Example No. Ar Y R 1) 3) 18) P-212 6-chloro- H COCF3 100 100 100 3-pyridyl P-213 2-chloro- H COCF3 100 100 100 5- thiazolyl P-215 6-chloro- 5- COCF3 100 80 75 3-pyridyl Cl P-216 6-chloro- 5-F COCF3 100 95 100 3-pyridyl P-218 2-chloro- 5- COCF3 100 60 5- Cl thiazolyl P-219 2-chloro- 5-F COCF3 80 85 5- thiazolyl P-222 6-chloro- 4- COCF3 100 100 3-pyridyl Me P-223 6-chloro- 5- COCF3 75 75 3-pyridyl Me P-225 4-chloro- H COCF3 90 phenyl P-226 3-pyridyl H COCF3 60 100 P-227 6-chloro- H COCF3 100 100 100 5-fluoro- 3-pyridyl P-228 6- H COCF3 30 95 100 trifluoromethyl- 3- pyridyl P-229 6-fluoro- H COCF3 100 100 100 3-pyridyl P-230 5,6- H COCF3 100 100 dichloro- 3-pyridyl P-231 6-bromo-3- H COCF3 100 100 100 pyridyl P-232 6-chloro- 4-F COCF3 80 3-pyridyl P-233 6-chloro- 3-F COCF3 100 75 3-pyridyl P-234 6-chloro- H COCHCl2 100 100 100 3-pyridyl P-235 6-chloro- H COCCl3 100 95 75 3-pyridyl P-236 6-chloro- H COCH2Cl 100 3-pyridyl P-238 6-chloro- H COCHF2 100 100 100 3-pyridyl P-239 6-chloro- H COCF2Cl 100 100 100 3-pyridyI P-240 6-chloro- H COCHClBr 100 100 3-pyridyl P-241 6-chloro- H COCHBr2 100 100 3-pyridyl P-242 6-chloro- H COCF2CF3 100 100 100 3-pyridyl P-243 2-chloro- H COCF3 100 100 100 5- pyrimidinyl P-244 6-chloro- H COCH2Br 100 100 3-pyridyl  1-20 6-chloro- H CSCF3 100 100 100 3-pyridyl  1-21 6-chloro- H CSCHF2 80 100 100 3-pyridyl  1-22 6-chloro- H CSCF2Cl 100 100 3-pyridyl  1-23 6-chloro- H CSCF2CF3 100 100 3-pyridyl  1-42 6-chloro- H C(═NOMe)CF3 100 100 100 3-pyridyl  1-150 6-chloro- H C(═NCH2CH2SMe)CF3 100 100 80 3-pyridyl 3-3 6-fluoro- H COCHF2 50 100 80 3-pyridyl 3-4 6-fluoro- H COCF2Cl 100 100 100 3-pyridyl 3-5 6-fluoro- H COCF2CF3 100 55 80 3-pyridyl  3-20 6-fluoro- H CSCF3 55 100 80 3-pyridyl 4-3 6-Bromo-3- H COCHF2 100 100 pyridyl 4-4 6-Bromo-3- H COCF2Cl 100 100 pyridyl 4-5 6-Bromo-3- H COCF2CF3 100 100 100 pyridyl  4-20 6-Bromo-3- H CSCF3 100 100 100 pyridyl 5-3 6Chloro- H COCHF2 100 100 5fluoro- 3pyridyl 5-4 6Chloro- H COCF2Cl 100 100 5fluoro- 3pyridyl  5-20 6Chloro- H CSCF3 100 100 5fluoro- 3pyridyl 6-3 2-Cl-5- H COCHF2 80 100 pyrimidinyl 6-4 2-Cl-5- H COCF3Cl 90 100 100 pyrimidiny 102-2  6-chloro- 3- COCF3 10 100 100 3-pyridyl CN

Effects Against Insecticide Resistant Pests Reference Test Example 19 Pest Control Test of Nilaparvata lugens

A rice seedling in pot culture was subjected to soil drench with a solution of the compound of Formula (I), which had been prepared so as to be a 10% acetone water. Three days after the treatment, ten second instar larvae of Nilaparvata lugens, which had been collected outdoors and proliferated indoors, were each released to the rice seedling. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Six days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. Test in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Furthermore, for comparison, the test against a species of Nilaparvata lugens which is highly susceptible to imidacloprid was performed by the same method as described above, and the results thereof are shown in Table 45. As described in Table 45, Compound P212 and Compound 1-20 exhibited high insecticidal effects against susceptible species and drug resistant species of Nilaparvata lugens, and the death rates of larvae at 0.005 mg/seedling were (susceptible species) 100% and 100%, (resistant population I) 95% and 77% and (resistant population II) 100% and 85%, respectively. Meanwhile, the death rates of imidacloprid at 0.05 mg/seedling were (susceptible species) 100%, (resistant population I) 38% and (resistant population II) 69%, and the insecticidal effect thereof was also low even at a high dose. From the above results, it became obvious that Compound P212 and Compound 1-20 have high insecticidal effects even against Nilaparvata lugens resistance against imidacloprid.

Further, for the origin of test pests, bugs collected outdoors from the Kumamoto prefecture (I) in 2007 and from the Fukuoka prefecture (II) in 2005 as resistant population of Nilaparvata lugens, and bugs collected from the Kagoshima prefecture and then successively reared indoors for a long time as the imidacloprid susceptible population of Nilaparvata lugens were used.

TABLE 56 Insecticidal effects against Nilaparvata lugens (death rate %) Effects against Nilaparvata lugens Susceptible Resistant Resistant population population I population II six days six days six days Throughput after the after the after the (mg/seedling) treatment treatment treatment P212 0.05 100 100 100 0.005 100 95 100 1-20 0.01 95 100 100 0.005 100 77 85 Imidacloprid 0.05 100 38 69 0.01 100 39

Mixed Agent Test Example Test Example 1 Soil Irrigation Treatment Test of Laodelphax striatella

A rice seedling in pot culture was subjected to soil drench treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 10% acetone water. After the rice seedling was left to stand for 3 days, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

In addition, when there was no synergistic effect, a theoretical value was calculated by the Colby's equation shown as follows, and the results are shown in the Table.

theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212 or Compound 1-20)

B: 100−(mortality of larvae or adults when treated only with each of imidacloprid, fipronil, chlorantraniliprole, spinosad, clothianidin, dinotefuran, sulfoxaflor, pymetrozine, thiamethoxam, flupyradifurone and cycloxaprid))

Method for Judging Synergistic Effects

When the mortality against Laodelphax striatella in the case of a mixture with another agent exceeded the theoretical value by the Colby's equation, a synergistic effect was judged to be present.

It was demonstrated that mixed agents of the insecticides of imidacloprid, fipronil, chlorantraniliprole, spinosad, clothianidin, dinotefuran, sulfoxaflor, pymetrozine, thiamethoxam, flupyradifurone and cycoxaprid, which were provided and tested as Compound P212, all show a mortality of larvae or adults, exceed the theoretical value and have synergistic effects.

In addition, it was demonstrated that mixed agents of the insecticides of imidacloprid and fipronil, which were provided and tested as Compound 1-20, all show a mortality of larvae or adults, exceed the theoretical value and have synergistic effects.

Furthermore, it was demonstrated that mixed agents of the fungicides of probenazole, isotianil, tiadinil and orysastrobin, which were provided and tested as Compound P212, all exhibit insecticidal effect equal to or higher than the insecticidal effect when treated with Compound P212 alone and may be mixed and treated with a fungicide. Likewise, it was demonstrated that mixed agents of the fungicide of probenazole, which was provided and tested as Compound 1-20, exhibit insecticidal effect equal to or higher than the insecticidal effect when treated with Compound 1-20 alone and may be mixed and treated with a fungicide.

<Example of Mixed Agent with Insecticide>

TABLE 57 Mortality (%) of single agent and mixed agent against Laodelphax striatella Rate Compound P212 Insecticide name mg/Seedling 0 0.005 — — 0 39 Imidacloprid 0.005 0 70 Fipronil 0.005 26 65 Chlorantraniliprole 0.05 9 60 Spinosad 0.5 0 62

TABLE 58 Theoretical value (%) by Colby's equation Rate Compound P212 Insecticide name mg/Seedling 0 0.005 — — 0 39 Imidacloprid 0.005 0 39 Fipronil 0.005 26 55 Chlorantraniliprole 0.05 9 44 Spinosad 0.5 0 39

TABLE 59 Mortality (%) of single agent and mixed agent against Laodelphax striatella Rate Compound P212 Insecticide name mg/Seedling 0 0.005 — — 0 18 Clothianidin 0.005 23 56 Dinotefuran 0.005 0 30 Sulfoxaflor 0.005 1 63 Pymetrozine 0.05 15 89

TABLE 60 Theoretical value (%) by Colby's equation Rate Compound P212 Insecticide name mg/Seedling 0 0.005 — — 0 18 Clothianidin 0.005 23 37 Dinotefuran 0.005 0 18 Sulfoxaflor 0.005 1 19 Pymetrozine 0.05 15 30

TABLE 61 Mortality (%) of single agent and mixed agent against Laodelphax striatella Rate Compound P212 Insecticide name mg/Seedling 0 0.005 — — 0 14 Thiamethoxam 0.01 23 45

TABLE 62 Theoretical value (%) by Colby's equation Rate Compound P212 Insecticide name mg/Seedling 0 0.005 — — 0 14 Thiamethoxam 0.01 23 34

TABLE 63 Mortality (%) of single agent and mixed agent against Laodelphax striatella Rate Compound P212 Insecticide name mg/Seedling 0 0.005 — — 0 45 Flupyradifurone 0.01 5 85

TABLE 64 Theoretical value (%) by Colby's equation Rate Compound P212 Insecticide name mg/Seedling 0 0.005 — — 0 45 Flupyradifurone 0.01 5 48

TABLE 65 Mortality (%) of single agent and mixed agent against Laodelphax striatella Rate Compound 1-20 Insecticide name mg/Seedling 0 0.005 — — 0 12 Imidacloprid 0.005 0 74 Fipronil 0.001 0 80

TABLE 66 Theoretical value (%) by Colby's equation Rate Compound 1-20 Insecticide name mg/Seedling 0 0.005 — — 0 12 Imidacloprid 0.005 0 12 Fipronil 0.001 0 12

TABLE 67 Mortality (%) of single agent and mixed agent against Laodelphax striatella Rate Compound P212 Insecticide name mg/Seedling 0 0.005 — — 0 0 Cycloxaprid 0.005 0 7

TABLE 68 Theoretical value (%) by Colby's equation Rate mg/ Compound P212 Insecticide name Seedling 0 0.005 — — 0 0 Cycloxaprid 0.005 0 0

TABLE 69 Mortality (%) of single agent and mixed agent against Laodelphax striatella Rate Compound Compound mg/ P212 1-20 Fungicide name Seedling 0 0.005 0 0.005 — — 0 39 0 8 Probenazole 0.5 9 59 9 65

TABLE 70 Theoretical value (%) by Colby's equation Rate Compound Compound mg/ P212 1-20 Fungicide name Seedling 0 0.005 0 0.005 — — 0 39 0 8 Probenazole 0.5 9 44 9 16

TABLE 71 Mortality (%) of single agent and mixed agent against Laodelphax striatella Rate Compound P212 Fungicide name mg/Seedling 0 0.005 — — 0 19 Isotianil 0.5 5 30 Tiadinil 0.5 8 30 Orysastrobin 0.5 4 70

TABLE 72 Theoretical value (%) by Colby's equation Rate Compound P212 Fungicide name mg/Seedling 0 0.005 — — 0 19 Isotianil 0.5 5 23 Tiadinil 0.5 8 25 Orysastrobin 0.5 4 22

Test Example 2 Foliar Treatment Test Against Laodelphax Striatella

A drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was foliar sprayed to a rice seedling in pot culture. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Further, when there was no synergistic effect, a theoretical value was calculated by the Colby's equation shown as follows, and the results are shown in the Table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212 or Compound 1-20)

B: 100−(mortality of larvae or adults when treated only with etofenprox or silafluofen))

Method for Judging Synergistic Effects

When the mortality against Laodelphax striatella in the case of a mixture with another agent exceeded the theoretical value by the Colby's equation, a synergistic effect was judged to be present.

It was demonstrated that mixed agents of the insecticides of etofenprox and silafluofen, which were provided and tested as Compound P212 or Compound 1-20, all show a mortality of larvae or adults approximately equal to the theoretical value, and may be mixed with the insecticide even in a foliar treatment-like usage.

TABLE 73 Mortality (%) of single agent and mixed agent against Laodelphax s striatella Compound Compound Insecticide Rate — P212 1-20 name (ppm) 0 0.625 0.625 — 0 95 90 Etofenprox 10 30 90 95 Silafluofen 5 55 100 100

TABLE 74 Theoretical value (%) by Colby's equation Compound Compound Insecticide Rate — P212 1-20 name (ppm) 0 0.625 0.625 — 0 95 90 Etofenprox 10 30 97 93 Silafluofen 5 55 98 95

Test Example 3 Pest Control Test of Aphis gossypii

A leaf disk having a diameter of 2.0 cm was cut out from a cucumber in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed thereto. After an air drying process, first instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

In addition, when there was no synergistic effect, a theoretical value was calculated by the Colby's equation shown as follows, and the results are shown in the Table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212 or Compound 1-20)

B: 100−(mortality of larvae or adults when treated only with afidopyropen)

Method for Judging Synergistic Effects

When the mortality against Aphis gossypii in the case of a mixture with another agent exceeded the theoretical value by the Colby's equation, a synergistic effect was judged to be present.

It was demonstrated that mixed agents of compounds of Formula (II), which were provided and tested as Compound P212 or Compound 1-20, all show a mortality of larvae or adults, exceed the theoretical value and have synergistic effects.

TABLE 75 Mortality (%) of single agent and mixed agent against Aphis gossypii Insecticide Rate Compound P212 Compound 1-20 name ppm 0 0.313 0 0.625 — — 0 45 0 19 Afidopyropen 0.002 25 70 25 40

TABLE 76 Theoretical value (%) by Colby's equation Insecticide Rate Compound P212 Compound 1-20 name ppm 0 0.313 0 0.625 — — 0 45 0 19 Afidopyropen 0.002 25 59 25 39

Test Example 4 Pest Control Test of Plutella xylostella

A leaf disk having a diameter of 5.0 cm was cut out from a cabbage in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed thereto. After an air drying process, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the mortality of larvae was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Furthermore, when there was no synergistic effect, a theoretical value was calculated by the Colby's equation shown as follows, and the results are shown in the Table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated with only Compound P212)

B: 100−(mortality of larvae or adults when treated with only flometoquin, spinosad, fipronil, chlorantraniliprole, 1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate, or afidopyropen))

Method for Judging Synergistic Effects

When the mortality against Plutella xylostella in the case of a mixture with another agent exceeded the theoretical value by the Colby's equation, a synergistic effect was judged to be present.

It was demonstrated that a mixed agent of the insecticide of flometoquin, which was provided and tested, with Compound P212, shows a death rate of larvae or adults, exceeds the theoretical value and has synergistic effects.

TABLE 77 Mortality (%) of single agent and mixed agent against Plutella xylostella Rate Compound P212 Insecticide name ppm 0 1.25 — — 0 0 Flometoquin 0.313 0 30

TABLE 78 Theoretical value (%) by Colby's equation Insecticide Rate Compound P212 name ppm 0 1.25 — — 0 0 Flometoquin 0.313 0 0

TABLE 79 Mortality (%) of single agent and mixed agent against Plutella xylostella Compound P212 Rate ppm Insecticide name 0 1.0 — 0 40 Afidopyropen Rate 10 20 70 Spinosad ppm 0.01 11 70

TABLE 80 Theoretical value (%) by Colby's equation Compound P212 Rate ppm Insecticide name 0 1.0 — 0 40 Afidopyropen Rate 10 20 52 Spinosad ppm 0.01 11 45

TABLE 81 Mortality (%) of single agent and mixed agent against Plutella xylostella Compound P212 Rate ppm Insecticide name 0 1.0 — 0 30 Afidopyropen Rate 5 0 80 ppm

TABLE 82 Theoretical value (%) by Colby's equation Compound P212 Rate ppm Insecticide name 0 1.0 — 0 30 Afidopyropen Rate 5 0 30 ppm

TABLE 83 Mortality (%) of single agent and mixed agent against Plutella xylostella Compound P212 Rate ppm Insecticide name 0 2.0 — 0 60 Fipronil Rate 0.04 50 100 Chlorantraniliprole ppm 0.002 60 100

TABLE 84 Theoretical value (%) by Colby's equation Compound P212 Rate ppm Insecticide name 0 2.0 — 0 60 Fipronil Rate 0.04 50 80 Chlorantraniliprole ppm 0.002 60 84

TABLE 85 Mortality (%) of single agent and mixed agent against Plutella xylostella Compound P212 Rate ppm Insecticide name 0 2.0 — 0 50 1-((6- Rate 1 30 70 chloropyridin- ppm 3-yl)methyl)-4- oxo-3-phenyl- 4H-pyrido[1,2- a]pyrimidin-1- ium-2-olate Afidopyropen 5 0 100

TABLE 86 Theoretical value (%) by Colby's equation Compound P212 Rate ppm Insecticide name 0 2.0 — 0 50 1-((6- Rate 1 30 65 chloropyridin- ppm 3-yl)methyl)-4- oxo-3-phenyl- 4H-pyrido[1,2- a]pyrimidin-1- ium-2-olate Afidopyropen 5 0 50

Test Example 5 Pest Control Test of Spodoptera litura

A leaf disk having a diameter of 5.0 cm was cut out from a cabbage in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed thereto. After an air drying process, third instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colby's equation given below, and the results are shown in the tables.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212)

B: 100−(mortality of larvae or adults when treated with only the insecticide chlorantraniliprole, emamectin benzoate, flometoquin, or afidopyropen))

Method for Judging Synergistic Effects

When the mortality against Spodoptera litura in the case of a mixture with another agent exceeded the theoretical value given by Colby's equation, a synergistic effect was judged to be present.

It was demonstrated that a mixed agent of the insecticide chlorantraniliprole, emamectin benzoate, flometoquin, or afidopyropen tested with Compound P212 shows a mortality for larvae or adults in excess of the theoretical value and has synergistic effects.

TABLE 87 Mortality (%) of single agent and mixed agent against Spodoptera litura (1) Compound P212 Rate ppm Insecticide name 0 20 — 0 40 Afidopyropen Rate 10 0 80 ppm

TABLE 88 Theoretical value (%) by Colby's equation Compound P212 Rate ppm Insecticide name 0 20 — 0 40 Afidopyropen Rate 10 0 40 ppm

TABLE 89 Mortality (%) of single agent and mixed agent against Spodoptera litura (2) Compound P212 Rate ppm Insecticide name 0 20 — 0 10 Chlorantraniliprole Rate 0.02 20 30 Emamectin benzoate ppm 0.02 0 20

TABLE 90 Theoretical value (%) by Colby's equation Compound P212 Rate ppm Insecticide name 0 20 — 0 10 Chlorantraniliprole Rate 0.02 20 28 Emamectin benzoate ppm 0.02 0 10

TABLE 91 Mortality (%) of single agent and mixed agent against Spodoptera litura (3) Compound P212 Rate ppm Insecticide name 0 50 — 0 10 Flometoquin Rate 5 10 20 Afidopyropen ppm 5 0 50

TABLE 92 Theoretical value (%) by Colby's equation Compound P212 Rate ppm Insecticide name 0 50 — 0 10 Flometoquin Rate 5 10 19 Afidopyropen ppm 5 0 10

Test Example 6 Pest Control Test of Frankliniella Occidentalis

A leaf disk having a diameter of 2.8 cm was cut out from the common bean in pot culture, and a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 50% acetone water (0.05% Tween20 available), was sprayed thereto. After an air drying process, first instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Three days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colby's equation given below, and the results are shown in the table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212)

B: 100−(mortality of larvae or adults when treated with only the insecticide imidacloprid, dinotefuran, or acetamiprid))

Method for Judging Synergistic Effects

When the mortality against Frankliniella occidentalis in the case of a mixture with another agent exceeded the theoretical value given by Colby's equation, a synergistic effect was judged to be present.

It was demonstrated that a mixed agent of the insecticide imidacloprid or dinotefuran tested with Compound P212 shows a mortality for larvae or adults in excess of the theoretical value and has synergistic effects.

TABLE 93 Mortality (%) of single agent and mixed agent against Frankliniella occidentalis(1) Compound P212 Rate ppm Insecticide name 0 10 — 0 69 Imidacloprid Rate 20 69 94 ppm

TABLE 94 Theoretical value (%) by Colby's equation Compound P212 Rate ppm Insecticide name 0 10 — 0 69 Imidacloprid Rate 20 69 90 ppm

TABLE 95 Mortality (%) of single agent and mixed agent against Frankliniella occidentalis(2) Compound P212 Rate ppm Insecticide name 0 20 — 0 70 Dinotefuran Rate 5 35 85 ppm

TABLE 96 Theoretical value (%) by Colby's equation Compound P212 Rate ppm Insecticide name 0 20 — 0 70 Dinotefuran Rate 5 35 81 ppm

Test Example 7 Soil Irrigation Treatment Test on Chilo Suppressalis

Rice seedlings in pot culture were submitted to a soil irrigation treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 10% acetone water. After standing for 3 days, second instar larvae were released thereto. This was followed by standing in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Six days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colby's equation given below, and the results are shown in the table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212)

B: 100−(mortality of larvae or adults when treated with only the insecticide fipronil, cyantraniliprole or spinosad))

Method for Judging Synergistic Effects

When the insecticidal effect (table) against Chilo suppressalis in the case of a mixture with another agent exceeded the theoretical value given by Colby's equation, a synergistic effect was judged to be present.

It was demonstrated that a mixed agent of the insecticide fipronil, cyantraniliprole or spinosad tested with Compound P212 shows a mortality for larvae or adults in excess of the theoretical value in both cases and has synergistic effects.

TABLE 97 Mortality (%) of single agent and mixed agent against Chilo suppressalis(1) Compound P212 Rate mg/seedling Insecticide name 0 0.01 — 0 33 Cyantraniliprole Rate mg/ 0.005 83 100 seedling

TABLE 98 Theoretical value (%) by Colby's equation Compound P212 Rate mg/seedling Insecticide name 0 0.01 — 0 33 Cyantraniliprole Rate mg/ 0.005 83 89 seedling

TABLE 99 Mortality (%) of single agent and mixed agent against Chilo suppressalis(2) Compound P212 Rate mg/seedling Insecticide name 0 0.002 — 0 40 Fipronil Rate mg/ 0.0005 40 80 Chlorantraniliprole seedling 0.0005 60 80 Spinosad 0.002 80 100

TABLE 100 Theoretical value (%) by Colby's equation Compound P212 Rate mg/seedling Insecticide name 0 0.002 — 0 40 Fipronil Rate mg/ 0.0005 40 64 Chlorantraniliprole seedling 0.0005 60 76 Spinosad 0.002 80 88

Test Example 8 Soil Irrigation Treatment Test on Naranga Aenescens

Rice seedlings in pot culture were subjected to a soil irrigation treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared so as to be a 10% acetone water. After standing for 3 days, first instar larvae were released thereto. This was followed by standing in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Five days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colby's equation given below, and the results are shown in the table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(mortality of larvae or adults when treated only with Compound P212)

B: 100−(mortality of larvae or adults when treated with only the insecticide spinosad or fipronil))

Method for Judging Synergistic Effects

When the mortality against Naranga aenescens in the case of a mixture with another agent exceeded the theoretical value given by Colby's equation, a synergistic effect was judged to be present.

It was demonstrated that a mixed agent of the insecticide spinosad or fipronil tested with Compound P212 shows a mortality for larvae or adults in excess of the theoretical value in all cases and has synergistic effects.

TABLE 101 Mortality (%) of single agent and mixed agent against Naranga aenescens Compound P212 Rate mg/seedling Insecticide name 0 0.01 — 0 60 Spinosad Rate mg/ 0.005 40 100 Fipronil seedling 0.01 20 80

TABLE 102 Theoretical value (%) by Colby's equation Compound P212 Rate mg/seedling Insecticide name 0 0.01 — 0 60 Spinosad Rate mg/ 0.005 40 76 Fipronil seedling 0.01 20 68

Test Example 9 Test on Callosobruchus Chinensis

A compound of Formula (I) and the insecticide indicated below, prepared in predetermined concentrations using acetone, were separately topically applied to the back of the same adult Callosobruchus chinensis. The Callosobruchus chinensis was then introduced into a plastic cup and held in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. One day after the release, the insects were observed for survival or death, and the insect mortality was calculated by the following equation. The test was performed in duplicate.

Insect mortality (%)={number of dead insects/(number of survived insects+number of dead insects)}×100

Furthermore, a theoretical value for the case of no synergistic effect was calculated using Colby's equation given below, and the results are shown in the table.

Theoretical value (%)=100−(A×B)/100  Colby's equation:

(A: 100−(insect mortality for treatment with only Compound P212)

B: 100−(insect mortality for treatment with only the insecticide fipronil or imidacloprid))

Method for Judging Synergistic Effects

When the mortality against Callosobruchus chinensis in the case of a mixture with another agent exceeded the theoretical value given by Colby's equation, a synergistic effect was judged to be present.

It was demonstrated that co-treatment with the insecticide fipronil or imidacloprid tested with Compound P212 shows an insect mortality in excess of the theoretical value in both cases and has synergistic effects.

TABLE 103 Mortality (%) of single agent and mixed agent against Callosobruchus chinensis Compound P212 Rate ng/head Insecticide name 0 0.2 — 0 20 Fipronil Rate ng/ 0.2 0 36 Imidacloprid head 0.2 40 60

TABLE 104 Theoretical value (%) by Colby's equation Compound P212 Rate ng/head Insecticide name 0 0.2 — 0 20 Fipronil Rate ng/ 0.2 0 20 Imidacloprid head 0.2 40 52

Test Example 10 Pest Control Test of Rice Blast

A rice seedling in pot culture was subjected to soil irrigation treatment with a drug solution of the compound of Formula (I) at a predetermined concentration, or a drug solution of a mixture of a compound of Formula (I) and an insecticide as indicated below at a predetermined concentration, which had been prepared with a 10% acetone water. Three days after the treatment, a spore suspension (2×10⁵ ea/mL, 0.05% Tween available) of rice blast bacteria was sprayed and inoculated thereto, and the rice seedling was placed in a moist chamber for 24 hours to promote infection. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Seven days after the inoculation, the number of lesions was measured, and the preventive value was calculated by the following equation. The test was performed in triplicate.

Preventive value={(number of lesions in a zone without treatment−number of lesions in a zone with treatment)/(number of lesions without treatment)}×100

As a result, it was demonstrated that in a throughput of probenazole at 0.125 mg/seedling, any one mixed agent of Compound P212 and Compound 1-20 exhibits insecticidal effect equal to the insecticidal effect when treated with probenazole alone and may be mixed and treated with a fungicide.

TABLE 105 Compound P212 Compound 1-20 Rate mg/seedling Insecticide name 0 2.5 0 2.5 — 0 3.3 0 52.5 Probenazole Rate mg/ 0.125 96.7 93.4 96.7 91.8 seedling

Test Example 11 Test of Rice Blast Control (Foliar Treatment)

Rice seedlings were treated by foliar application with a drug solution of the compound of Formula (I), or a drug solution of a mixture of a compound of Formula (I) and the fungicide indicated below, prepared in a predetermined concentration with 10% acetone water. After the treatment, a rice blast spore suspension (1.5×10⁵ ea/mL, 0.05% Tween available) was sprayed and inoculated thereto followed by holding in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. Fourteen days after the inoculation, the number of lesions was measured, and the preventive value was calculated by the following equation. The test was performed in triplicate.

Preventive value={(number of lesions in a zone without treatment−number of lesions in a zone with treatment)/(number of lesions in a zone without treatment)}×100

As a result, it was demonstrated that at a treatment concentration of 0.5 ppm using tiadinil, isotianil, orysastrobin, tricyclazole, diclocymet, tebufloquin, azoxystrobin or kasugamycin, the mixed agent with Compound P212 also exhibits a fungicidal effect equal to that for treatment with tiadinil, isotianil, orysastrobin, tricyclazole, diclocymet, tebufloquin, azoxystrobin or kasugamycin alone and a mixed treatment with a fungicide is therefore possible.

TABLE 106 (Rice blast test 1) Compound P212 Rate ppm Fungicide name 0 50 — 0 4 Tiadinil Rate 0.5 0 18 Isotianil ppm 0.5 66 72

TABLE 107 (Rice blast test 2) Compound P212 Rate ppm Fungicide name 0 50 — 0 16 Orysastrobin Rate 0.5 20 91 Tricyclazole ppm 0.5 72 92 Diclocymet 0.5 8 52 Tebufloquin 0.5 48 72

TABLE 108 (Rice blast test 3) Compound P212 Rate ppm Fungicide name 0 50 — 0 0 Azoxystrobin Rate 0.5 37 35 Kasugamycin ppm 0.5 0 37

Test Example 12 Test of Control of Rice Sheath Blight (Rhizoctonia solani)

Six weeks after planting, rice seedlings were subjected to foliar spray treatment with a drug solution of the compound of Formula (I), or a drug solution of a mixture of a compound of Formula (I) and a fungicide as indicated below, prepared in a predetermined concentration with 10% acetone water. After an air drying process, a plug of growing Rhizoctonia solani (1.0 cm² agar square each) was allowed to stand at the base of the rice. This was followed by holding in a thermostatic chamber (30° C. day −25° C. night, 16 hours of light period-8 hours of dark period). Six days after the inoculation, the lesion height was measured, and the preventive value was calculated by the following equation. The test was performed in duplicate.

Preventive value={(lesion height in a zone without treatment−lesion height in a zone with treatment)/(lesion height in a zone without treatment)}×100

As a result, it was demonstrated that, at a treatment concentration of 5 ppm using thifluzamide, furametpyr, pencycuron, azoxystrobin, simeconazole, validamycin, or orysastrobin, the mixed agent with ppm Compound P212 presented the same fungicidal effect as for treatment with thifluzamide, furametpyr, pencycuron, azoxystrobin, simeconazole, validamycin, or orysastrobin alone, and mixed treatment with a fungicide is therefore possible.

TABLE 109 (Sheath blight test 1) Compound P212 Rate ppm Fungicide name 0 50 — 0 14 Thifluzamide Rate 5 92 97 Furametpyr ppm 5 77 94 Pencycuron 5 69 77

TABLE 110 (Sheath blight test 2) Compound P212 Rate ppm Fungicide name 0 50 — 0 9 Azoxystrobin Rate 5 95 100 Simeconazole ppm 5 5 24 Validamycin 5 32 74 Orysastrobin 5 72 59

Test Example 13 Test with Laodelphax striatellus by Treatment During the Vegetative Phase

Rice was planted in nursery boxes and emergence was carried out for three days a 30° C. followed by transfer of the nursery boxes to a glass greenhouse at 25° C. During the vegetative phase five days after planting, the nursery boxes were treated with a prescribed amount of a mixed granule of 0.24 mg/mg probenazole (24%) and 0.02 mg/mg Compound P212 (2%). The rice seedlings were transplanted to 1/5000a Wagner pots 22 days after planting and were grown in a greenhouse at 25° C. Second instar larvae of Laodelphax striatellus were released at 13, 26, and 38 days post-transplantation to the Wagner pots; this was followed by holding in a glass greenhouse at 25° C. Five days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%) {number of dead larvae/(number of survived larvae+number of dead larvae)}×100

According to the results, it was shown that the mixed granule of probenazole and Compound P212 presented a high insecticidal effect of 100% mortality and exhibited control at a practical level.

Test Example 14 Test with Laodelphax striatellus by Soil Irrigation Treatment

Rice seedlings in pot cultivation were subjected to a soil irrigation treatment with a drug solution of a compound of Formula (I) or a drug solution of a mixture of a compound of Formula (I) and a paddy herbicide as indicated below, prepared in predetermined concentrations so as to be a 10% acetone water. After standing for three days, second instar larvae were released thereto. Thereafter, the larvae were left to stand in a thermostatic chamber (16 hours of light period-8 hours of dark period) at 25° C. five days after the release, the larvae were observed for survival or death, and the larvae mortality was calculated by the following equation. The test was performed in duplicate.

Mortality of larvae (%)={number of dead larvae/(number of survived larvae+number of dead larvae)}×100

The mixed agent of Imazosulfuron, cafenstrole, cyhalofop-butyl, daimuron and pyrazolate tested with the Compound P212 was shown in all instances to exhibit an insecticidal effect at least equal to that for treatment with Compound P212 by itself, and a mixed treatment with a herbicide is thus possible.

TABLE 111 Compound P212 Rate mg/seedling Herbicide name 0 0.005 0.01 — 0 0 100 Imazosulfuron Rate 0.05 0 0 100 Cafenstrole mg/ 0.05 0 0 100 Cyhalofop- seedling 0.05 0 0 100 butyl Daimuron 0.05 0 0 100 Pyrazolate 0.05 0 0 100

Test Example 15 Test of the Control of Haemaphysalis longicornis

A capsule with a diameter of 2 cm and a height of 2 cm was attached to the dorsal surface of a mouse. A compound of Formula (I), ivermectin, moxidectin, permethrin, amitraz, fipronil, spinetram and the mixture of the compound of Formula (I) and each insecticide were dissolved in ethanol at the concentrations given in Table O, and each of these was dripped onto the surface of a mouse body within a capsule. After thorough drying, eight Haemaphysalis longicornis nymphs were released and the top of the capsule was sealed with a lid. The mouse was kept in a cage at 25° C. using a 12-hour light period and a 12-hour dark period. Five days after the release, the capsule was removed and the number of surviving and dead nymphs and the number of engorged individuals were counted and the insect mortality and agonal rate was calculated by the following equation.

Insect mortality and agonal rate (%)={number of dead and agonal insects/(number of survived insects+number of dead and agonal insects)}×100

The results showed that, at a rate of 0.009 μg of ivermectin or moxidectin, the mixed agent of either with Compound P212 also gave a tick control effect that was the same as treatment with ivermectin, moxidectin, permethrin, amitraz, fipronil and spinetram alone and mixed treatment with ivermectin, moxidectin, permethrin, amitraz, fipronil and spinetram is thus possible.

TABLE 112 Mortality (%) of single agent and mixed agent against Haemaphysalis longicornis (1) Compound P212 Rate μg Insecticide name 0 1.18 — 0 53 Ivermectin Rate 0.009 3 53 Moxidectin μg 0.009 6 44

TABLE 113 Mortality (%) of single agent and mixed agent against Haemaphysalis longicornis (2) Compound P212 Rate μg Insecticide name 0 1.18 — 0 60 Amitraz Rate 0.38 41 90 Permethrin μg 9.5 71 86

TABLE 114 Theoretical value (%) by Colby's equation Compound P212 Rate μg Insecticide name 0 1.18 — 0 60 Amitraz Rate 0.38 41 77 Permethrin μg 9.5 71 88

TABLE 115 Mortality (%) of single agent and mixed agent against Haemaphysalis longicornis (3) Compound P212 Rate μg Insecticide name 0 1.18 — 0 38 fipronil Rate 0.38 78 93 spinetoram μg 0.38 6 22

TABLE 116 Theoretical value (%) by Colby's equation Compound P212 Rate μg Insecticide name 0 1.18 — 0 38 fipronil Rate 0.38 78 86 spinetoram μg 0.38 6 41

TABLE 117 Mortality (%) of single agent and mixed agent against Haemaphysalis longicornis (4) Compound P212 Rate μg Insecticide name 0 1.18 — 0 18 pyriproxyfen Rate 0.0475 2 44 spinosad μg 1.9 2.5 43

TABLE 118 Theoretical value (%) by Colby's equation Compound P212 Rate μg Insecticide name 0 1.18 — 0 18 pyriproxyfen Rate 0.0475 2 20 spinosad μg 1.9 2.5 20

TABLE 119 Mortality (%) of single agent and mixed agent against Haemaphysalis longicornis (5) Compound P212 Rate μg Insecticide name 0 1.18 — 0 23 imidacloprid Rate 1.9 7.7 60 dinotefuran μg 1.9 0

TABLE 120 Theoretical value (%) by Colby's equation Compound P212 Rate μg Insecticide name 0 1.18 — 0 23 imidacloprid Rate 1.9 7.7 32 dinotefuran μg 1.9 0 25 

1-24. (canceled)
 25. A pest control composition comprising: at least one iminopyridine derivative selected from the group consisting of N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide and acid addition salts thereof; and at least one insecticide selected from the group consisting of imidacloprid, dinotefuran, flometoquin, and agriculturally and/or zootechnically acceptable acid addition salts thereof; wherein the at least one iminopyridine derivative: the at least one insecticide is in a range from 0.1 to 80% by weight: 0.1 to 80% by weight.
 26. A method for protecting plants or animals from pests comprising simultaneously or independently applying the pest control composition of claim 25 to a region to be treated.
 27. A method for protecting plants or animals from pests by treating pests, plants, seeds of plants, soil, cultivation carriers or animals as a target, with an effective amount of the pest control composition of claim
 25. 28. A pest control composition comprising: at least one iminopyridine derivative selected from the group consisting of N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide and acid addition salts thereof; and at least one other pest control agent, wherein the other pest control agent is a control agent for animal parasitic pests and is selected from the group consisting of imidacloprid, dinotefuran, and agriculturally and/or zootechnically acceptable acid addition salts thereof; wherein the at least one iminopyridine derivative: the control agent for animal parasitic pests is in a range from 0.1 to 80% by weight: 0.1 to 80% by weight.
 29. The pest control composition according to claim 25, wherein the pest is at least one selected from the group consisting of Frankliniella occidentalis, Laodelphax striatella, Aphis gossypii, Plutella xylostella; Spodoptera litura, Chilo suppressalis, Callosobruchus chinensis and Haemaphysalis longicornis.
 30. The pest control composition according to claim 28, wherein the pest is at least one selected from the group consisting of Frankliniella occidentalis, Laodelphax striatella, Aphis gossypii, Plutella xylostella; Spodoptera litura, Chilo suppressalis, Callosobruchus chinensis and Haemaphysalis longicornis.
 31. A method for protecting plants or animals from pests according to claim 26, wherein the pest is at least one selected from the group consisting of Frankliniella occidentalis, Laodelphax striatella, Aphis gossypii, Plutella xylostella; Spodoptera litura, Chilo suppressalis, Callosobruchus chinensis and Haemaphysalis longicomis.
 32. A method for protecting plants or animals from pests according to claim 27, wherein the pest is at least one selected from the group consisting of Frankliniella occidentalis, Laodelphax striatella, Aphis gossypii, Plutella xylostella; Spodoptera litura, Chilo suppressalis, Callosobruchus chinensis and Haemaphysalis longicomis. 